Pyrimidinone derivatives and herbicides containing them

ABSTRACT

Pyrimidinone derivatives of the general formula:                    
     wherein R 1  is hydrogen or alkyl; R 2  is haloalkyl; R 3  is nitrogen or CH; G is optionally substituted ethylene, trimethylene, or vinylene; and Q is selected from several optionally substituted or heterocyclic-condensed phenyl groups, are useful as the active ingredients of herbicides because of their excellent herbicidal activity.

FILED OF INVENTION

The present invention relates to pyrimidinone derivatives and their use.

OBJECT OF THE INVENTION

It is an object of the present invention to provide compounds with excellent herbicidal activity.

SUMMARY OF THE INVENTION

The present inventors have intensively studied to seek out various compounds with excellent herbicidal activity. As a result, they have found that pyrimidinone derivatives of the general formula as depicted below have excellent herbicidal activity, thereby completing the present invention.

Thus the present invention provides pyrimidinone derivatives of the general formula:

(hereinafter referred to as the present compound(s))

wherein:

R¹ is hydrogen or C₁-C₃ alkyl;

R² is C₁-C₃ haloalkyl;

R³ is nitrogen or CH;

G is any group of the general formula:

wherein:

E¹, E², E³, E⁴, E⁵, E⁶, E⁷, E⁸, E⁹, E¹⁰, E¹¹, and E¹² are independently hydrogen or C₁-C₃ alkyl; and

Q is any group of the general formula:

wherein:

X is hydrogen or halogen;

Y is halogen, nitro, cyano, or trifluoromethyl;

Z¹ is oxygen, sulfur, NH, or CH₂;

n is 0 or 1;

R⁴ is hydrogen or C₁-C₃ alkyl;

R⁵ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, (C₃-C₈ cycloalkyl) C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₃ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, hydroxy C₁-C₆ alkyl, —CH₂CON(R¹²)R¹³, —CH₂COON(R¹²)R¹³, —CH(C₁-C₄ alkyl)CON(R¹²)R¹³, or —CH(C₁-C₄ alkyl)COON(R¹²)R¹³,

wherein:

R¹² and R¹³ are independently hydrogen, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₂-C₆ alkyl, (C₁-C₆ alkyl)carbonylamino C₂-C₆ alkyl, hydroxy C₂-C₆ alkyl, optionally substituted benzyl, optionally substituted phenyl, or {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, or R¹² and R¹³ are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene, or ethylenethioethylene;

and

B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR¹⁰, SR¹⁰, SO₂OR²¹, N(R¹²)R¹³,SO₂N(R¹²)R¹³,NR¹²(COR⁹), NR¹²(SO₂R²⁸), N(SO₂R²⁸)(SO₂R²⁹), N(SO₂R²⁸)(COR⁹), NHCOOR¹¹, CONR¹²R¹³, CSNR¹²R¹³, COR³⁰, CR²³═CR²⁴COR³⁰, CR²³═CR²⁴CON(R¹²)R¹³, CH₂CHWCON(R¹²)R¹³, CR³⁰═NOR³¹, CR³⁰═NN(R¹²)R¹³,CR³⁰(Z²R³²)₂, OCO₂R³², OCOR³², COOR²², CH₂OR¹⁰, CR²³═CR²⁴COOR²⁵, or CH₂CHWCOOR²⁵,

wherein:

R¹² and R¹³ are as defined above;

W is hydrogen, chlorine, or bromine;

Z² is oxygen or sulfur;

R⁹ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl;

R¹¹ is hydrogen, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl;

R²⁸ and R²⁹ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, or phenyl;

R³⁰ is hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, or C₃-C₆ alkynyl;

R³¹ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)-carbonyl C₁-C₆ alkyl, or {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl;

R³² is hydrogen, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl;

R¹⁰ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)-carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkyl) C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl, —CH₂COON—(R¹²)R¹³,—CH(C₁-C₄ alkyl)COON(R¹²)R¹³,—CH₂CON(R¹²)R¹³, —CH(C₁-C₄ alkyl)CON(R¹²)R¹³ (wherein R¹² and R¹³ are as defined above), C₂-C₆ alkenyloxycarbonyl C₁-C₆ alkyl, C₃-C₆ haloalkenyloxycarbonyl C₁-C₆ alkyl, C₃-C₆ alkynyloxycarbonyl C₁-C₆ alkyl, C₃-C₆ haloalkynyloxycarbonyl C₁-C₆ alkyl, (C₁-C₆ alkylthio)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkylthio)-carbonyl C₁-C₆ alkyl, (C₃-C₆ alkenylthio)carbonyl C₁-C₆ alkyl, (C₃-C₆ haloalkenylthio)carbonyl C₁-C₆ alkyl, (C₃-C₆ alkynylthio)carbonyl C₁-C₆ alkyl, (C₃-C₆ haloalkynylthio)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkylthio)carbonyl C₁-C₆ alkyl, (C₃-C₈ cyclohaloalkylthio)carbonyl C₁-C₆ alkyl, ((C₃-C₈ cycloalkyl) C₁-C₆ alkylthio)carbonyl C₁-C₆ alkyl, di(C₁-C₆ alkyl)C═NO carbonyl C₁-C₆ alkyl, (optionally substituted benzylthio)-carbonyl C₁-C₆ alkyl, (optionally substituted phenylthio)-carbonyl C₁-C₆ alkyl, hydroxy C₂-C₆ alkoxycarbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₂-C₆ alkoxycarbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonylamino C₂-C₆ alkoxycarbonyl C₁-C₆ alkyl, {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₃-C₈ cycloalkoxycarbonyl, C₃-C₆ alkenyloxycarbonyl, optionally substituted benzyloxycarbonyl, C₁-C₆ alkylcarbonyl, optionally substituted benzyloxycarbonyl C₁-C₆ alkyl, optionally substituted phenoxycarbonyl C₁-C₆ alkyl, optionally substituted furyloxycarbonyl C₁-C₆ alkyl, optionally substituted furyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted thienyloxycarbonyl C₁-C₆ alkyl, optionally substituted thienyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrrolyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrrolyloxy C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted imidazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted imidazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted thiazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted thiazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted oxazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted oxazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted isothiazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted isothiazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted isoxazoyloxycarbonyl C—CC alkyl, optionally substituted isoxazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyradinyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyradinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyriaidinyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrimidinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted yridazinyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridazinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolidinyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolidinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted indazolyloxycarbonyl C₁-C₆ alkyl, optionally substituted indazolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted quinolyloxycarbonyl C₁-C₆ alkyl, optionally substituted quinolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted isoquinolyloxycarbonyl C₁-C₆ alkyl, or optionally substituted isoquinolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, or a group of the general formula:

wherein:

R¹⁴ is hydrogen or C₁-C₅ alkyl; and

R¹⁵ is hydrogen, hydroxyl, or a group of —O—COR¹⁶,

wherein:

R¹⁶ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₈ cycloalkyl, optionally substituted phenyl, optionally substituted benzyl, or C₁-C₆ alkoxy;

or a group of the general formula:

wherein:

R¹⁷ is hydrogen, halogen, or C₁-C₆ alkyl; and

R¹⁸ is C₃-C₈ cycloalkyl, benzyl, C₂-C₁₀ alkyl with an epoxy group, C₃-C₈ cycloalkyl C₁-C₆ alkyl, C₃-C₈ cycloalkyl C₂-C₆ alkenyl, carboxy C₂-C₆ alkenyl, (C₁-Cs alkoxy)carbonyl C₂-C₆ alkenyl, (C₁-C₈ haloalkoxy)carbonyl C₂-C₆ alkenyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₂-C₆ alkenyl, (C₃-C₈ cycloalkoxy)-carbonyl C₂-C₆ alkenyl, C₁-C₆ alkyl substituted with OR¹⁹ and OR²⁰ on the same carbon atom, C₂-C₆ alkenyl substituted with OR¹⁹ and OR²⁰ on the same carbon atom, C₁-C₆ alkyl substituted with SR¹⁹ and SR²⁰ on the same carbon atom, or C₂-C₆ alkenyl substituted with SR¹⁹ and SR²⁰ on the same carbon atom,

wherein:

R¹⁹ and R²⁰ are independently C₁-C₆ alkyl, C₁-Cr haloalkyl, or R¹⁹ and R²⁰ are taken together to form ethylene optionally substituted with halogen, trimethylene optionally substituted with halogen, tetramethylene optionally substituted with halogen, pentamethylene optionally substituted with halogen, or ethyleneoxyethylene optionally substituted with halogen;

R²¹ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-Cs cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, or benzyl;

R²² is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)-carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkyl, {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, hydroxy C₁-C₆ alkyl, —CH₂—COON(R²⁶)R²⁷, —CH(C₁-C₄ alkyl) COON(R²⁶)R²⁷,—CH₂CON—(R²⁶)R²⁷, or —CH(C₁-C₄ alkyl)CON(R²⁶)R²⁷,

wherein:

R²⁶ and R²⁷ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)-carbonyl C₁-C₆ alkyl, or {(C₁-C₄ alkoxy) C₁-C₄ alkyl)-carbonyl C₁-C₆ alkyl, or R²⁶ and R²⁷ are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene; R²³ and R²⁴ are independently hydrogen or C₁-C₆ alkyl; and R²⁵ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl; and herbicides containing them as active ingredients.

DETAILED DESCRIPTION OF THE INVENTION

The C₁-C₃ alkyl represented by R¹ may include methyl and ethyl.

The C₁-C₃ haloalkyl represented by R² may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, and 1,1-difluoroethyl.

The C₁-C₃ alkyl represented by E¹, E², E³, E⁴, E⁵, E⁶, E⁷, E⁸, E⁹, E¹⁰E¹¹, or E¹² may include methyl, ethyl, propyl, and isopropyl.

The halogen represented by B may include fluorine, chlorine, bromine, and iodine.

The halogen, represented by X or Y may include fluorine, chlorine, bromine, and iodine.

The C₁-C₃ alkyl represented by R⁴ may include methyl and ethyl.

The C₁-C₆ alkyl represented by R⁵ may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl (wherein “t-” means “tertiary-” and this is hereinafter used in the same meaning), and isoamyl.

The C₁-C₆ haloalkyl represented by R⁵ may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, and difluoromethyl.

The (C₃-C₈ cycloalkyl) C₁-C₆ alkyl represented by R⁵ may include cyclopentylmethyl.

The C₃-C₆ alkenyl represented by R⁵ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ haloalkenyl represented by R⁵ may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

The C₃-C₆ alkynyl represented by R⁵ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, and 1,1-dimethyl-2-propynyl.

The C₃-C₆ haloalkynyl represented by R⁵ may include 3-iodo-2-propynyl and 3-bromo-2-propynyl.

The cyano C₁-C₆ alkyl represented by R⁵ may include cyanomethyl and cyanoethyl.

The C₁-C₄ alkoxy C₁-C₄ alkyl represented by R⁵ may include methoxymethyl, 1-methoxyethyl, and ethoxyethyl.

The C₁-C₃ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl represented by R⁵ may include methoxymethoxymethyl, methoxyethoxymethyl, and ethoxymethoxymethyl.

The carboxy C₁-C₆ alkyl represented by R⁵ may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

The (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented by R⁵ may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, and 1-isoamyloxycarbonylethyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R⁵ may include methoxyethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.

The (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R⁵ may include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

The hydroxy C₁-C₆ alkyl represented by R⁵ may include hydroxymethyl, hydroxyethyl, and hydroxypropyl.

The C₁-C₄ alkylthio C₁-C₄ alkyl represented by R⁵ may include methylthiomethyl, 1-methylthioethyl, and ethylthiomethyl. s The C₁-C₆ alkyl represented by R⁹ may include methyl, ethyl, and isopropyl.

The C₁-C₆ haloalkyl represented by R⁹ may include chloromethyl, trichloromethyl, and trifluoromethyl.

The C₃-C₈ cycloalkyl represented by R⁹ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R⁹ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₁-C₆ alkyl represented by R¹⁰ may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

The C₁-C₆ haloalkyl represented by R¹⁰ may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, and 2,2,2-trifluoroethyl.

The C₃-C₈ cycloalkyl represented by R¹⁰ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R¹⁰ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ haloalkenyl represented by R¹⁰ may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

The C₃-C₆ alkynyl represented by R¹⁰ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

The C₃-C₆ haloalkynyl represented by R¹⁰ may include 3-bromopropargyl.

The cyano C₁-C₆ alkyl represented by R¹⁰ may include cyanomethyl.

The C₁-C₄ alkoxy C₁-C₄ alkyl represented by R¹⁰ may include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

The C₁-C₄ alkylthio C₁-C₄ alkyl represented by R¹⁰ may include methylthiomethyl and methylthioethyl.

The carboxy C₁-C₆ alkyl represented by R¹⁰ may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

The (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl represented by R¹⁰ may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R¹⁰ may include methoxymethoxycarbonylmethyl, methoxyethoxycarbonylmethyl, and 1-methoxyethoxycarbonylethyl.

The (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R¹⁰ may include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

The C₁-C₆ alkoxycarbonyl represented by R¹⁰ may include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and t-butoxycarbonyl.

The C₁-C₆ haloalkoxycarbonyl represented by R¹⁰ may include 2,2,2-trichloroethoxycarbonyl.

The C₃-C₈ cycloalkoxycarbonyl represented by RI⁰ may include cyclopropyloxycarbonyl and cyclobutyloxycarbonyl.

The C₃-C₆ alkenyloxycarbonyl represented by R¹⁰ may include allyloxycarbonyl.

The {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl represented by R¹⁰ may include (methoxycarbonyl)methoxycarbonylmethyl and (ethoxycarbonyl)methoxycarbonylmethyl.

The C₁-C₆ alkyl represented by R¹¹ may include methyl, ethyl, and isopropyl.

The C₃-C₈ cycloalkyl represented by R¹¹ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R¹¹ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₁-C₆ alkyl represented by R¹² or R¹³ may include methyl, ethyl, propyl, isopropyl, butyl, and isobutyl.

The C₃-C₈ cycloalkyl represented by R¹² or R¹³ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₁-C₆ haloalkyl represented by R¹² or R¹³ may include fluoroethyl, chloroethyl, and bromoethyl.

The C₃-C₆ alkenyl represented by R¹² or R¹³ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ alkynyl represented by R¹² or R¹³ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

The cyano C₁-C₆ alkyl represented by R¹² or R¹³ may include cyanomethyl and cyanoethyl.

The C₁-C₄ alkoxy C₁-C₄ alkyl represented by R¹² or R¹³ may include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

The C₁-C₄ alkylthio C₁-C₄ alkyl represented by R¹² or R¹³ may include methylthiomethyl and methylthioethyl.

The carboxy C₁-C₆ alkyl represented by R¹² or R¹³ may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

The (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented by R¹² or R¹³ may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isoporpoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycabronylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

The (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R¹² or R¹³ may include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

The (C₁-C₆ alkyl)carbonyloxy C₂-C₆ alkyl represented by R¹² or R¹³ may include methylcarbonyloxyethyl and ethylcarbonyloxyethyl.

The (C₁-C₆ alkyl)carbonylamino C₂-C₆ alkyl represented by R¹² or R¹³ may include methylcarbonylaminoethyl and ethylcarbonylaminoethyl.

The hydroxy C₂-C₆ alkyl represented by R¹² or R¹³ may include hydroxyethyl and hydroxypropyl.

The optionally substituted benzyl represented by R¹² or R¹³ may include benzyl.

The optionally substituted phenyl represented by R¹² or R¹³ may include phenyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl represented by R¹² or R¹³ may include methoxymethylcarbonylmethyl and 1-methoxymethoxycarbonylethyl.

The C₁-C₅ alkyl represented by R¹⁴ may include methyl and ethyl.

The C₁-C₆ alkyl represented by R¹⁶ may include methyl, ethyl, and isopropyl.

The C₁-C₆ haloalkyl represented by R¹⁶ may include trichloromethyl and trifluoromethyl.

The C₃-C₆ alkenyl represented by R¹⁶ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₈ cycloalkyl represented by R¹⁶ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The optionally substituted phenyl represented by R¹⁶ may include phenyl.

The optionally substituted benzyl represented by R¹⁶ may include benzyl.

The C₁-C₆ alkoxy represented by R¹⁶ may include methoxy and ethoxy.

The halogen represented by R¹⁷ may include fluorine, chlorine, bromine, and iodine.

The C₁-C₆ alkyl represented by R¹⁷ may include methyl, ethyl, and isopropyl.

The C₃-C₈ cycloalkyl represented by R¹⁸ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₂-C₁₀ alkyl with an epoxy group represented by R¹⁸ may include 2-oxyranyl and 2-oxyranylmethyl.

The C₃-C₈ cycloalkyl C₁-C₆ alkyl represented by R¹⁸ may include cyclopentylmethyl, cyclohexylmethyl, and cyclopropylethyl.

The C₃-C₈ cycloalkyl C₂-C₆ alkenyl represented by R¹⁸ may include 3-cyclopentylallyl.

The C₁-C₆ alkyl substituted with OR¹⁹ and OR²⁰ on the same carbon atom, which is represented by R¹⁸, may include —CH(OR¹⁹)(OR²⁰) and —CH₂—CH(OR¹⁹)(OR²⁰).

The C₁-C₆ alkyl substituted with SR¹⁹ and SR²⁰ on the same carbon atom, which is represented by R¹⁸, may include —CH(SR¹⁹)(SR²⁰) and —CH₂—CH(SR¹⁹)(SR²⁰).

The carboxy C₂-C₆ alkenyl represented by R¹⁸ may include 3-carboxyallyl.

The (C₁-C₈ alkoxy)carbonyl C₂-C₆ alkenyl represented by R¹⁸ may include 3-methoxycarbonylallyl and 3-ethoxycarbonylallyl.

The (C₁-C₈ haloalkoxy)carbonyl C₂-C₆ alkenyl represented by R¹⁸ may include 3-(2-fluoroethoxy)carbonylallyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₂-C₆ alkenyl represented by R¹⁸ may include 3-(2-methoxyethoxy)carbonylallyl.

The C₁-C₆ alkyl represented by R¹⁹ or R²⁰ may include methyl, ethyl, propyl, isopropyl, butyl, and isobutyl.

The C₁-C₆ haloalkyl represented by R¹⁹ or R²⁰ may include 2-chloroethyl and 2-fluoroethyl.

The C₁-C₆ alkyl represented by R²¹ may include methyl and ethyl.

The C₁-C₆ haloalkyl represented by R²¹ may include fluoroethyl, chloroethyl, and bromoethyl.

The C₃-C₈ cycloalkyl represented by R²¹ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R²¹ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ haloalkenyl represented by R²¹ may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

The C₃-C₆ alkynyl represented by R²¹ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

The C₃-C₆ haloalkynyl represented by R²¹ may include 3-bromopropargyl.

The C₁-C₆ alkyl represented by R²² may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

The C₁-C₆ haloalkyl represented by R²² may include 2-chloroethyl, 2-bromoethyl, and 2,2,2-trifluoroethyl.

The C₃-C₈ cycloalkyl represented by R²² may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R²² may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ haloalkenyl represented by R²² may include 2-chloro-2-propenyl, and 3,3-dichloro-2-propenyl.

The C₃-C₆ alkynyl represented by R²² may include propargyl, 1-methyl-2-propynyl, and 2-butynyl.

The C₃-C₆ haloalkynyl represented by R²² may include 3-bromopropargyl.

The cyano C₁-C₆ alkyl represented by R²² may include cyanoethyl.

The C₁-C₄ alkoxy C₁-C₄ alkyl represented by R²² may include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

The C₁-C₄ alkylthio C₁-C₄ alkyl represented by R²² may include methylthioethyl.

The carboxy C₁-C₆ alkyl represented by R²² may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

The (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl represented by R²² may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

The (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl represented by R²² may include chloroethoxycarbonylmethyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R²² may include methoxymethoxycarbonylmethyl, methoxyethoxycarbonylmethyl, and 1-methoxyethoxycarbonylethyl.

The (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R²² may include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

The C₁-C₆ alkyl represented by R²³ or R²⁴ may include methyl and ethyl.

The C₁-C₆ alkyl represented by R²⁵ may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

The C₁-C₆ haloalkyl represented by R²⁵ may include 2-chloroethyl, 2-bromoethyl, and 2,2,2-trifluoroethyl.

The C₃-C₈ cycloalkyl represented by R²⁵ may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R²⁵ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₁-C₆ alkyl represented by R²⁶ or R²⁷ may include methyl, ethyl, propyl, and isopropyl.

The C₁-C₆ haloalkyl represented by R²⁶ or R²⁷ may include chloroethyl and bromoethyl.

The C₃-C₆ alkenyl represented by R²⁶ or R²⁷ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ alkynyl represented by R²⁶ or R²⁷ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

The cyano C₁-C₆ alkyl represented by R²⁶ or R²⁷ may include cyanomethyl and cyanoethyl.

The C₁-C₄ alkoxy C₁-C₄ alkyl represented by R²⁶ or R²⁷ may include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

The C₁-C₄ alkylthio C₁-C₄ alkyl represented by R²⁶ or R²⁷ may include methylthiomethyl and methylthioethyl.

The carboxy C₁-C₆ alkyl represented by R²⁶ or R²⁷ may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

The (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented by R²⁶ or R²⁷ may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

The (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R²⁶ or R²⁷ may include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl represented by R²⁶ or R²⁷ may include methoxymethylcarbonylmethyl and 1-methoxymethylcarbonylethyl.

The C₁-C₆ alkyl represented by R²⁸ or R²⁹ may include methyl, ethyl, propyl, and isopropyl.

The C₁-C₆ haloalkyl represented by R²⁸ or R²⁹ may include chloromethyl and chloroethyl.

The C₁-C₆ alkyl represented by R³⁰ may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

The C₃-C₆ alkenyl represented by R³⁰ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ alkynyl represented by R³⁰ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

The C₁-C₆ alkyl represented by R³¹ may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

The C₁-C₆ haloalkyl represented by R³¹ may include 2-chloroethyl, 2-bromoethyl, and 2,2,2-trifluoroethyl.

The C₃-C₆ alkenyl represented by R³ may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

The C₃-C₆ haloalkenyl represented by R³¹ may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

The C₃-C₆ alkynyl represented by R³¹ may include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

The cyano C₁-C₆ alkyl represented by R³¹ may include cyanomethyl.

The C₂-C₈ alkoxyalkyl represented by R³¹ may include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

The C₂-C₈ alkylthioalkyl represented by R³¹ may include methylthiomethyl and methylthioethyl.

The carboxy C₁-C₆ alkyl represented by R³¹ may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

The (C₁-C₆ alkoxy)carbonyl Cr-C₆ alkyl represented by R³¹ may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

The (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R³¹ may include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, cyclobutyloxycarbonylethyl, cyclopentyloxycarbonylethyl, and cyclohexyloxycarbonylethyl.

The {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R³¹ may include methoxymethoxycarbonylmethyl, methoxyethoxycarbonylmethyl, and 1-methoxyethoxycarbonylethyl.

The C₁-C₆ alkyl represented by R³² may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

The C₃-C₈ cycloalkyl represented by R³² may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ alkenyl represented by R³² may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

For the present compounds, there may exist geometrical isomers based on the double bond, and optical isomers or diastereomers based on the asymmetric carbon atom. These isomers and their mixtures are included in the present compounds.

In the present compounds, the substituent groups preferred in view of herbicidal activity may include fluorine-substituted methyl (e.g., trifluoromethyl, chlorodifluoromethyl) and fluorine-substituted ethyl (e.g., pentafluoroethyl, 1,1-difluoroethyl) for R^(2; and Q-)1, and Q-2, for Q. When Q is Q-1, compounds with hydrogen or fluorine for X and chlorine for Y are more preferred. When Q is Q-2, compounds with fluorine or hydrogen for X, oxygen for Z¹, hydrogen for R⁴, and n=1 are more preferred. In these compounds, still more preferred are those which further have C₃-C₆ alkynyl for R⁵. Compounds with a combination of the above preferred substituent groups are more preferred in view of herbicidal activity.

The following are specific examples of the preferred compounds of the present invention in view of herbicidal activity. The numbers in parentheses after the compound names are corresponding to the compound numbers in Tables 1 to 248 below.

7-Fluoro-6-[7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one (2-26)

6-[7-Oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one (2-25)

6-Fluoro-5-[7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one (2-164)

5-[7-Oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one (2-163)

8-(4-Chloro-2-fluoro-5-methoxyphenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one (1-262)

8-(4-Chloro-2-fluoro-5-ethoxyphenyl)-5-trifluoromethyl-2,3,7,8-tetra-3hydroimidazo [1,2-a] pyrimidin-7-one (1-268)

8-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one (1-274)

8-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one (1-340)

8-(4-Chloro-2-fluoro-5-(1-methylpropargyloxy)phenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one (1-346)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid methyl ester (1-400)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy} acetic acid ethyl ester (1-406)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid isopropyl ester (1-430)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid methyl ester (1-454)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid ethyl ester (1-460)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid isopropyl ester (1-484)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid methyl ester (1-706)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid ethyl ester (1-712) 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid methyl ester (1-760)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid ethyl ester (1-766)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid methyl ester (1-166)

(2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid ethyl ester (1-172)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid methyl ester (1-214)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid ethyl ester (1-220)

N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenyl}methanesulfonamide (1-88)

N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenyl}chloromethanesulfonamide (1-100)

N-{2-Chloro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenyl}methanesulfonamide (1-86)

2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)benzoic acid methyl ester (1-952)

2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)benzoic acid ethyl ester (1-958)

2-Chloro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid methyl ester (1-950)

2-Chloro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid ethyl ester (1-956)

7-Fluoro-6-[7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one (7-26)

6-[7-Oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one (7-25)

6-Fluoro-5-[7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one (7-164)

5-[7-Oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one (7-163)

8-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-7-one (6-274)

8-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-7-one (6-340)

8-(4-Chloro-2-fluoro-5-(1-methylpropargyloxy)phenyl)-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-7-one (6-346)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid methyl ester (6-400)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid ethyl ester (6-406)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid isopropyl ester (6-430)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid methyl ester (6-454) 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid ethyl ester (6-460)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid isopropyl ester (6-484)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid methyl ester (6-706)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid ethyl ester (6-712)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid methyl ester (6-760)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid ethyl ester (6-766)

(2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid methyl ester (6-166)

{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid ethyl ester (6-172)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid methyl ester (6-214)

2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid ethyl ester (6-220)

N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenyl}methanesulfonamide (6-88)

N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-ajpyrimidin-8-yl)phenyl}chloromethanesulfonamide (6-100)

N-{2-Chloro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]-pyrimidin-8-yl)phenyl}methanesulfonamide (6-86)

2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)benzoic acid methyl ester (6-952)

2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)benzoic acid ethyl ester (6-958)

2-Chloro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid methyl ester (6-950)

2-Chloro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid ethyl ester (6-956)

The present compounds can be produced, for example, according to the following production processes 1 to 16.

Production Process 1

This is the production process in which an aniline derivative of the general formula:

wherein G, Q, and R³ are as defined above, is reacted with an ester derivative of the general formula:

wherein R¹ and R² are as defined above and R³³ is C₁-C₆ alky, or an acrylic acid derivative of the general formula:

wherein R¹, R², and R³³ are as defined above and R⁸⁰ is a leaving group such as C₁-C₆ alkoxy, C₁-C₆ alkylthio, di(C₁-C₃ alkyl)amino, halogen, C₁-C₆ alkylsulfonyl, or arylsulfonyl.

The reaction is usually effected without any solvent or in a solvent. The reaction temperature is usually in the range of 50° C. to 200° C. The reaction time is usually in the range of 1 to 100 hours.

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the ester derivative or acrylic acid derivative of the above general formula for 1 mole of the aniline derivative of the above general formula, although they may suitably be changed with the reaction conditions.

The solvent which can be used may include aliphatic hydrocarbons such as hexane, heptane, octane, and ligroin; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene;

ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof. Furthermore, acids such as p-toluenesulfonic acid may be used as the catalyst in the reaction.

After completion of the reaction, the reaction mixture is concentrated without further treatment, or the reaction mixture is poured into water, which is extracted with an organic solvent, and the organic layer is subjected to ordinary post-treatments such as drying and concentration. If necessary, purification may be carried out by an ordinary technique such as recrystallization or column chromatography. Thus the desired present compound can be obtained.

Production Process 2

This is the production process according to the following scheme:

wherein R⁵¹ is as defined for R⁵ but not hydrogen; R¹, R², R³,R⁴, R³³, X, and G are as defined above; and D is chlorine, bromine, iodine, methanesulfonyloxy, or p-toluenesulfonyloxy.

The reactions in the respective steps can be effected, for example, by the procedures as described in the Japanese Laid-open Patent Publication No. 1-301679, or by the following procedures.

1) Procedure for preparing compound [II] from compound [I]

Compound [II] can be prepared by reacting compound [I] with a nitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles for 1 mole of compound [I]

Solvent: sulfuric acid or the like

Temperature: −10° C. to room temperature

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [III] from compound [II]

Compound [III] can be prepared by reacting compound [II] with a compound of HOCH(R⁴)COOR³³ (wherein R⁴ and R³³ are as defined above) in the presence of potassium fluoride in a solvent.

Amount of compound of HOCH(R⁴)COOR³³: 1 to 50 moles for 1 mole of compound [II]

Amount of potassium fluoride: 1 to 50 moles for 1 mole of compound

Solvent: 1,4-dioxane or the like

Temperature: room temperature to heating temperature under reflux

Time: a moment to 96 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [IV] from compound [III]

Compound [IV] can be prepared by reducing compound [III] with iron powder or the like in the presence of an acid in a solvent.

Amount of iron powder or the like: 3 moles to an excessive amount for 1 mole of compound [III]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles for 1 mole of compound [III]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to heating temperature under reflux

Time: a moment to 24 hours

After completion of the reaction, the iron powder or the like is removed by filtration, and the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

4) Procedure for preparing compound [V] from compound [IV]

Compound [V] can be prepared by reacting compound [IV] with a compound of R⁵′-D (wherein R⁵¹ and D are as defined as above).

The reaction is usually effected in the presence of a base in a solvent.

The reaction temperature is usually in the range of −20° C. to 150° C., preferably 0° C. to 50° C. The reaction time is usually in the range of a moment to 48 hours.

The amounts of reagents to be used in the reaction are usually 1 to 3 moles of the compound of R⁵¹-D and usually 1 to 2 moles of the base, both for 1 mole of compound [IV].

The base which can be used in the reaction may include, for example, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate, and sodium carbonate; and organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

The solvent which can be used in the reaction may include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol adimethyl ether; nitro compounds such as nitrobenzene; acid amides such as N,N-dimethylformamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured into water, if necessary, and then subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as column chromatography or recrystallization. Thus the present compound [V] can be isolated.

Compound [III] can also be prepared according to the following scheme:

wherein R¹, R², R³, R⁴, X, G, and R³ are as defined above.

The reaction conditions in the respective steps are, for example, as follows:

1) Procedure for preparing compound [VII] from compound [VI]

Compound [VII] can be prepared by reacting compound [VI] with a compound of BrCH(R⁴)COOR³³ (wherein R⁴ and R³ are as defined above) in the presence of a base in a solvent.

Amount of compound of BrCH(R⁴)COOR³³: 1 to 2 moles for 1 mole of compound [VI]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 2 moles for 1 mole of compound [VI]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° C. to 100° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallzation. Thus the desired compound can be isolated.

2) Procedure for preparing compound [III) from compound [VII]

Compound [III] can be prepared by reacting compound [VII] with a nitrating agent in a solvent

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles for 1 mole of compound [VII]

Solvent: sulfuric acid, acetic acid, or the like

Temperature: −10° C. to room temperature

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [VIII] from compound [VI]

Compound [VIII] can be prepared by reacting compound [VI] with a nitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles for 1 mole of compound [VI]

Solvent: nitric acid, acetic acid, or the like

Temperature: −10° C. to room temperature

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an -p organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

4) Procedure for preparing compound [III] from compound [VIII]

Compound [III] can be prepared by reacting compound [VII] with a compound of BrCH(R⁴)COOR³³ (wherein R⁴ and R³³ are as defined above) in the presence of a base in a solvent.

Amount of compound of BrCHR⁴)COOR³³: 1 to 2 moles for 1 mole of compound [VIII]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 2 moles for 1 mole of compound [VIII]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° C. to 100° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 3

This is the production process according to the following scheme:

wherein X, R¹, R²,R³,G, R⁵¹, and D are as defined above.

The reactions in the respective steps can be effected, for example, by the procedures as described in the Japanese Laid-open Patent Publication No. 62-252787, or by the following procedures.

1) Procedure for preparing compound M] from compound [IX]

Compound [X] can be prepared by reducing compound [IX] with iron powder or the like in the presence of an acid in a solvent.

Amount of iron powder or the like: 3 moles to an excessive amount for 1 mole of compound [IX]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles for 1 mole of compound [IX]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to heating temperature under reflux

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [XI] from compound [X]

Compound [XI] can be prepared by reacting compound [X] with sodium thiocyanate, potassium thiocyanate, or the like in a solvent, and then with bromine or chlorine in a solvent.

Amount of sodium thiocyanate, potassium thiocyanate, or the like: 1 to 10 moles for 1 mole of compound []

Amount of bromine or chlorine: 1 to 10 moles for 1 mole of compound [X]

Solvent: aqueous hydrochloric acid, aqueous acetic acid, aqueous sulfuric acid, or the like

Temperature: 0° C. to 50° C.

Time: a moment to 150 hours

After completion of the reaction, the reaction mixture is poured into water, which is neutralized with an alkali, if necessary, and then extracted with an organic solvent. The organic layer is subjected to post-treatments such as drying and concentration. If necessary, purification may be carried out by an ordinary technique such as recrystallization or column chromatography. Thus the desired present compound can be obtained.

3) Procedure for preparing compound XII] from compound [XI]

Compound [XII] can be prepared by i) reacting compound [XI] with sodium nitrite, potassium nitrite, or the like in a solvent (reaction 1), and ii) subsequently heating in an acidic solution (reaction 2).

Reaction 1

Amount of sodium nitrite, potassium nitrite, or the like: 1 to 2 moles for 1 mole of compound [XI]

Solvent: aqueous hydrochloric acid or aqueous sulfuric acid

Temperature: −10° C. to 10° C.

Time: a moment to 5 hours

Reaction 2

Acidic solution: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: 70° C. to heating temperature under reflux

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

4) Procedure for preparing compound [XIII] from compound

Compound [XIII] can be prepared by reacting compound [XII] with a compound of R⁵′-D (wherein R⁵¹ and D are as defined above) in the presence of a base in a solvent.

Amount of compound of R⁵¹-D: 1 to 3 moles for 1 mole of compound [XII]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 2 moles for 1 mole of compound [XII]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° C. to 100° C.

Time: a moment to 48 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 4

This is the production process according to the following scheme:

wherein X, R¹, R², R³, G, and R⁵ are as defined above.

The reactions in the respective steps can be effected, for example, by the procedures as described in the Japanese Laid-open Patent Publication No. 61-165384, or by the following procedures.

1) Procedure for preparing compound [XV] from compound

Compound [XV] can be prepared by reducing compound [XIV] with iron powder or the like in the presence of an acid in a solvent.

Amount of iron powder or the like: 3 moles to an excessive amount for 1 mole of compound [XIV]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles for 1 mole of compound [XIV]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to heating temperature under reflux

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [XI] from compound [XV]

Compound [XVI] can be prepared by i) reacting compound [XV] with a nitrite in a solvent to give a diazonium salt (reaction 1), and ii) subsequently raising the temperature to cause circularization of the diazonium salt in a solvent (reaction 2).

Reaction 1

Nitrite: sodium nitrite, potassium nitrite, or the like

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: −10° C. to 10° C.

Time: a moment to 5 hours

Reaction 2

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: room temperature to 80° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 5

This is the production process according to the following scheme:

wherein Y¹ is as defined for Y but not nitro, and X, Y, R¹, R², R³, and G are as defined above.

The reactions in the respective steps can be effected, for example, by the procedures as described in the Japanese Laid-open Patent Publication No. 63-41466 or Published Specification of International Patent Application, No. WO92/11244, or by the following procedures. 1) Procedure for preparing compound P[VIII] from compound [XVII]

Compound [XVIII] can be prepared by adding nitric acid to compound [XVII] in a solvent (see Organic Synthesis Collective Vol. 1, p. 372).

The reaction temperature is usually in the range of 0° C. to 100° C. The reaction time is usually in the range of a moment to 24 hours.

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the nitric acid for 1 mole of compound [XVII], although they may suitably be changed with the reaction conditions.

The solvent which can be used may include acidic solvents such as sulfuric acid.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [XIX] from compound [XVIII]

Compound [XIX] can be prepared by reducing compound [XVIII] in a solvent (see Organic Synthesis Collective Vol. 2, p. 471, Vol. 5, p. 829.

The reaction can be effected, for example, by adding compound [XVIII] neat or dissolved in a solvent such as ethyl acetate to a mixture of acetic acid, iron powder, and water. The reaction temperature is usually in the range of 0° C. to 100° C. The reaction time is usually in the range of a moment to 24 hours.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 6

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, G, and D are as defined above; R³⁴ is as defined for R¹⁰ but not hydrogen; R³⁵ and R³⁶ are the same or different and are as defined for R¹² but not hydrogen, for COR⁹, for SOR²⁸, for SO₂R²⁹, or for COOR¹¹ but not carboxyl; the wordings “R³⁵-D or (R³⁵)₂O”, “R³⁶-D or (R³⁶)₂O”, and “R³⁴-D or (R³⁴)₂O” mean that the reaction can be effected with either of the compounds recited, depending upon the reaction conditions.

1) Procedure for preparing compound [XX] from compound [XXXII]

Compound [XX] can be prepared by i) reacting compound [XXXII] with a nitrite in a solvent (reaction 1), and ii) subsequently heating in an acidic solvent (reaction 2).

Reaction 1

Nitrite: sodium nitrite, potassium nitrite, or the like

Amount of nitrite: 1 to 2 moles for 1 mole of compound [XXII]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: −10° C. to 10° C.

Time: a moment to 5 hours

Reaction 2

Acid solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: 70° C. to heating temperature under reflux

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [XXIII] from compound [XX]

Compound [XXIII] can be prepared by reacting compound [XX] with a compound of R³⁴-D or (R³⁴)₂O (wherein R³⁴ and D are as defined as above) in the presence of a base in a solvent.

The reaction is usually effected in a solvent. The reaction temperature is usually in the range of −20° C. to 150° C., preferably 0° C. to 100° C. The reaction time is usually in the range of a moment to 72 hours.

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the compound of R³⁴-D or the compound of (R³⁴)₂O and 1 mole of the base, both for 1 mole of compound [XX], although they may suitably be changed with the reaction conditions.

The base which can be used in the reaction may include organic bases and inorganic bases such as potassium carbonate, sodium hydroxide, and sodium hydride.

The solvent which can be used in the reaction may include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halo-genated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide (hereinafter referred to as DMF), and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured into water, if necessary, and then subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as column chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [XXI] from compound [XXXII]

Compound [XXI] can be prepared by reacting compound [XII] with a compound of R³⁵-D or a compound of (R³⁵)₂O without any solvent or in a solvent, and if necessary, in the presence of a base.

The reaction temperature is usually in the range of −20° C. to 200° C., preferably 0° C. to 180° C. The reaction time is usually in the range of a moment to 72 hours.

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the compound of R³⁵-D or the compound of (R³⁵)2O and 1 mole of the base, both for 1 mole of compound [XXXII], although they may suitably be changed with the reaction conditions.

The base which can be used in the reaction may include organic bases such as pyridine and triethylamine and inorganic bases such as potassium carbonate.

The solvent which can be used in the reaction may include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halo-genated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, DMF, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

After completion of the reaction, the precipitated crystals are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

4) Procedure for preparing compound [XXII] from compound [XXI]

Compound [XXII] can be prepared by reacting compound [XXI] with a compound of R³⁶-D or a compound of (R³⁶)₂O. The reaction can be effected by the above procedure for preparing compound [XXI] from compound

Production Process 7

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, G, R¹², R¹³, and R²¹ are as defined above.

The reaction conditions in the respective steps are, for example, as follows:

1) Procedure for preparing compound [XXV] from compound [XXIV]

Compound [XXV] can be prepared by reacting compound [XXIV] with chlorosulfonic acid without any solvent or in a solvent (see Organic Synthesis Collective Vol. 1, 8 (1941)).

Amount of chlorosulfonic acid: 1 mole to an excessive amount for 1 mole of compound [XXIV]

Solvent: sulfuric acid

Temperature: 0° C. to 70° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [XXVI] from compound [XXV]

Compound [XXVI] can be prepared by reacting compound [XXVI] with a compound of R²′-OH (wherein R²¹ is as defined above) in the presence of a base without any solvent or in a solvent.

Amount of compound of R²¹-OH: 1 mole to an excessive amount for 1 mole of compound [XXV]

Base: tertiary amines such as triethylamine, inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles for 1 mole of compound [XXV]

Solvent: DMF, 1,4-dioxane, or the like

Temperature: 0° C. to 100° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [XXVII] from compound [XXV]

Compound [VII] can be prepared by reacting compound [XXV] with a compound of R¹²R¹³NH (wherein R¹² and R¹³ are as defined above) in the presence or absence of a base without any solvent or in a solvent.

Amount of compound of R¹²R¹³NH: 1 mole to an excessive amount for 1 mole of compound [XXV]

Base: tertiary amines such as triethylamine, inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles for 1 mole of compound [XXV]

Solvent: DMF, 1,4-dioxane, or the like

Temperature: 0° C. to 100° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 8

This is the production process according to the following scheme:

wherein X, Y, G, R¹, R², R³, R²³, R²⁴, R²⁵, R¹², and R¹³ are as defined above.

The reaction conditions in the respective steps are, for example, as follows:

1) Procedure for preparing compound [XXIX] from compound [XIII]

Compound [XXIX] can be prepared from compound [XXVIII] by the procedures as described in the Japanese Laid-open Patent Publication No. 5-294920.

2) Procedure for preparing compound [XXX] from compound [XXIX]

Compound [XXX] can be prepared by reacting compound [XXIX] with a compound of (C₆H₅)₃P═CR²⁴COOR²⁵ or a compound of (C₂H₅O)₂P(O)CHR²⁴—COOR²⁵ (wherein R²⁴ and R²⁵ are as defined above) in a solvent, and when the compound of (C₂H₅O)₂P(O)CHR²⁴COOR²⁵ is used, the reaction is effected in the presence of a base.

Amount of compound of (C₆H₅)₃P═CR²⁴COOR²⁵ or compound of (C₂H₅O)₂P(O)CHR²⁴COOR²⁵: 1 to 2 moles for 1 mole of compound [XXIX]

Solvent: THF, toluene, or the like

Base: sodium hydride or the like

Amount of base: 1 to 2 moles for 1 mole of compound [XXIX]

Temperature: 0° C. to 50° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [XXXI] from compound [XXX]

Compound [XXI] can be prepared by reacting compound [XXX] with a compound of R¹²R¹³NH.

Amount of compound of R¹²R¹³NH: 1 mole to an excessive amount for 1 mole of compound

Solvent: THF or the like

Temperature: 0° C. to 100° C.

Time: a moment to 24 hours

After completion of the reaction, the reaction mixture is poured into water, if necessary, and then subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as column chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 9

This is the production process according to the following scheme:

wherein X, Y, G, R¹, R², R³, and R²⁵ are as defined above and W is chlorine or bromine.

1) Procedure for preparing compound [XXXIII] from compound [XXXII]

The reactions in the respective steps can be effected, for example, by the procedures as described in the specification of U.S. Pat. No. 5,208,212, or by the following procedures.

Compound [XXXIII] can be prepared by i) converting compound [XXXII] into a diazonium salt by the ordinary method in a solvent such as aqueous hydrochloric acid, aqueous hydrobromic acid,, and aqueous sulfuric acid (reaction 1), and ii) subsequently reacting the diazonium slat with a compound of CH₂═CHCO₂R²⁵ (wherein R²⁵ is as defined above) in the presence of a copper salt such as copper(II) chloride or copper(II) bromide in a solvent such as acetonitrile (reaction 2).

Reaction 1

Diazotizing agent: sodium nitrite, potassium nitrite, or the like

Amount of diazotizing agent: 1 to 2 moles for 1 mole of compound [XXXII]

Temperature: −10° C. to 10° C.

Time: a moment to 5 hours

Reaction 2

Amount of compound of CH₂═CHCO₂R²⁵: 1 to 2 moles for 1 mole of compound [XXXII]

Amount of copper(II) chloride or copper(II) bromide: 1 mole to an excessive amount for 1 mole of compound [XXXII]

Temperature: −20° C. to 150° C., preferably 0° C. to 60° C.

Time: a moment to 72 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 10

This is the production process according to the following scheme:

wherein W³ is bromine or iodine, and X, Y, G, R¹, R², R³, and R²² are as defined above.

The reaction conditions in the respective steps are, for example, as follows:

1) Procedure for preparing compound [XXXIV] from compound [XXXII]

Compound [XXXIV] can be prepared by i) diazotizing compound [XXXII] in a solvent (reaction 1), and ii) subsequently reacting the diazonium salt with potassium iodide or copper(I) bromide in a solvent (reaction 2) (see Organic Synthesis Collective Vol. 2, 604 (1943), Vol. 1, 136 (1932)).

Reaction 1

Diazotizing agent: sodium nitrite, potassium nitrite, or the like

Amount of diazotizing agent: 1 to 2 moles for 1 mole of compound

Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or the like

Temperature: −10° C. to 10° C.

Time: a moment to 5 hours

Reaction 2

Amount of potassium iodide or copper(I) bromide: 1 mole to an excessive amount for 1 mole of compound [XXXII]

Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or the like

Temperature: 0° C. to 80° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [XXXV] from compound [XXXIV]

Compound [XXXV] can be prepared by reacting compound [XXXIV] with carbon monoxide and a compound of R²²—OH (wherein R²² is as defined above) in the presence of a transition metal catalysis and a base in a solvent under an atmosphere of carbon monoxide (see Bull. Chem. Soc. Jpn., 48(7), 2075(1975)).

Catalyst: PdCl₂(PPh₃)₂ (wherein Ph is phenyl) or the like

Amount of catalyst: a catalytic amount to 0.5 mole for 1 mole of compound [XXXIV]

Amount of compound of R²²—OH: 1 mole to an excessive amount for 1 mole of compound [XXXIV]

Base: organic bases such as diethylamine

Amount of base: 1 to 2 moles for 1 mole of compound [XXXIV]

Solvent: DMF or the like

Pressure of carbon monoxide: 1 atm to 150 atm

Temperature: 0° C. to 100° C.

Time: a moment to 72 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 11

This is the production process according to the following scheme:

wherein X, Y, G, R¹, R², and R³ are as defined above and R³⁷ is C₁-C₆ alkyl.

Compound [XXXVII] can be prepared by hydrolyzing compound [XXXVI] in the presence of an acid such as sulfuric acid, or by treating compound [XXXVI] with an acid such as boron tribromide in a solvent such as methylene chloride and then with water.

The reaction temperature is usually in the range of −20° C. to 150° C., preferably 0° C. to 100° C. The reaction time is usually in the range of a moment to 72 hours.

The amount of acid to be used in the reaction is stoichiometrically 1 mole for 1 mole of compound [XXXVI], although it may suitably be changed with the reaction conditions.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 12

This is the production process according to the following scheme:

wherein X, Y, G. R¹, R², R³, and Z² are as defined above; R³⁸ is hydrogen or C₁-C₆ alkyl; R³⁹ is hydrogen or C₁-C₆ alkyl; Z³ is oxygen or sulfur; R⁴⁰ is C₁-C₆ alkyl, C₃-C₆ alkenyl, or C₃-C₆ alkynyl.

Compound [XXXIX] can be prepared by reacting compound [XXXVIII] with a compound of R⁴⁰Z³H (wherein R⁴⁰ and Z³ are as defined above) in the presence or absence of a catalyst and usually in a solvent.

The amount of the compound of R⁴⁰Z³H to be used in the reaction is stoichiometrically 1 mole for 1 mole of compound [XXXVIII], although it may suitably be changed with the reaction conditions.

The catalyst which can be used may include p-toluenesulfonic acid. The solvent which can be used may include toluene, xylene, and compounds of R⁴⁰Z³H.

The reaction temperature is usually in the range of 0° C. to 200° C., preferably 50° C. to 150° C. The reaction time is usually in the range of a moment to 72 hours.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 13

This is the production process according to the following scheme:

wherein X, Y, G, R¹, R², and R³ are as defined above.

The reaction conditions in the respective steps are, for example, as follows:

1) Procedure for preparing compound [XL] from compound [XXXVII]

Compound [XL] can be prepared by reacting compound [XXXII] with 2,3-dichloropropene in the presence of a base in a solvent.

Amount of 2,3-dichloropropene: 1 to 3 moles for 1 mole of compound [XXXVII]

Base: inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles for 1 mole of compound [XXXVII]

Solvent: DMF or the like

Temperature: 0° C. to 70° C.

Time: a moment to 24 hours

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 14

This is the production process according to the following scheme:

wherein W¹ is halogen, preferably chlorine; R⁴³ is hydrogen or C₁-C₅ alkyl; and X, Y, G, Z², R¹, R²,R³, R¹², R¹³, R³¹, and R³² are as defined above.

The reaction conditions in the respective steps are, for example, as follows:

1) Procedure for preparing compound CLIXI from compound [XXVIII]

Compound [XLIX] can be prepared by reacting compound [XXVIII] with a halogenating agent such as thionyl chloride by the ordinary method in a solvent.

2) Procedure for preparing compound [L] from compound [XLIX]

Compound [L] can be prepared by reacting compound [XLIX] with a compound of the general formula:

wherein M⁺ is an alkali metal cation, preferably lithium cation or sodium cation; R⁴⁴ and R⁴⁵ are independently C₁-C₆ alkyl; and R⁴³ is as defined above to give a compound of the general formula:

wherein X, Y, R¹, R², R³, G, R⁴³, R⁴⁴, and R⁴⁵ are as defined above (reaction 1), and then hydrolyzing and decarboxylating this compound (reaction 2).

Reaction 1 is usually effected in a solvent. The reaction temperature is usually in the range of −20° C. to 50° C., preferably room temperature. The reaction time is usually in the range of a moment to 72 hours.

The solvent which can be used may include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol dimethyl ether; acid amides such as formamide, DMF, and acetamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

After completion of the reaction, the reaction mixture is concentrated, and the residue is subjected to reaction 2.

Reaction 2 is effected in the presence of sulfuric acid, hydrobromic acid, or the like in a solvent, e.g., lower carboxylic acids such as acetic acid, or without any solvent.

The reaction temperature is usually in the range of 80° C. to 140° C., preferably 100° C. to 120° C. The reaction time is usually in the range of a moment to 72 hours.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [LI] from compound [L]

Compound [LI] can be prepared by reacting compound [L] with H₂N—O—R³¹ (wherein R³¹ is as defined above).

The reaction is effected in a lower alcohol (e.g., methanol, ethanol, isopropanol) or in a mixed solution of a lower alcohol and water. The reaction temperature is usually in the range of 0° C. to 80° C. The reaction time is usually in the range of a moment to 72 hours.

The amount of the compound of H₂N—O—R³¹ to be used in the reaction is stoichiometrically 1 mole for 1 mole of compound [L], although it may suitably be changed with the reaction conditions.

The compound of H₂N—O—R³¹ can be used in the form of a free base or in the form of an acid addition salt such as hydrochloride salt or sulfate salt.

The reaction can also be effected with the addition of an organic base such as pyridine; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal hydrogencarbonate such as sodium hydrogencarbonate; or alkaline earth metal carbonate such as calcium carbonate.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Compound [LI] can also be prepared by reacting a compound of the general formula:

wherein G, X, Y, R¹, R², R³, and R⁴³ are as defined above, which is prepared by the procedure as described in the section 3) of Production Process 15, with a compound of R⁴⁹-D (wherein R⁴⁹ is as defined for R³¹ but not hydrogen and D is as defined above) in the presence of a base and usually in a solvent.

The base which can be used may include alkali metal alcoholates and alkali metal hydrides (e.g., sodium hydride).

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the compound of R⁴⁹-D and 1 to 2 moles of base, both for 1 mole of the compound of the above general formula, although they may suitably be changed with the reaction conditions.

The solvent which can be used may include ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol dimethyl ether; acid amides such as formamide, DMF, and acetamide; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; and mixtures thereof The reaction temperature is usually an integer of −10° C. to 100° C., preferably 0° C. to 80° C. The reaction time is usually an integer of a moment to 72 hours.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

4) Procedure for preparing compound [LII] from compound [L]

Compound [LII] can be prepared by reacting compound [L] with a compound of H₂N—N(R¹²)R¹³ (wherein R¹² and R¹³ are as defined above).

The reaction is effected in a lower alcohol (e.g., methanol, ethanol, isopropanol) or in a mixed solution of a lower alcohol and water. The reaction temperature is usually in the range of 0° C. to 80° C. The reaction time is usually in the range of a moment to 72 hours.

The amount of the compound of H₂N—N(R¹²)R¹³ to be used in the reaction is stoichiometrically 1 mole for 1 mole of compound [L], although it may suitably be changed with the reaction conditions.

The compound of H₂N—N(R¹²)R¹³ can be used in the form of a free base or in the form of an acid addition salt such as hydrochloride salt or sulfate salt.

The reaction can also be effected with the addition of a basic catalyst, e.g., an organic base such as pyridine; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal hydrogencarbonate such as sodium hydrogencarbonate; or alkaline earth metal carbonate such as calcium carbonate.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

5) Procedure for preparing compound [LIII] from compound [L]

Compound [LIII] can be prepared by reacting compound [L] with a compound of R³²Z²H (wherein Z² and R³² are as defined above) usually in the presence of a catalytic amount to an excessive amount of an acid such as p-toluenesulfonic acid, hydrochloric acid, or sulfuric acid in an organic solvent such as benzene or chloroform.

The amount of the compound of R³²Z²H to be used in the reaction is stoichiometrically 2 moles for 1 mole of compound [L], although it may suitably be changed with the reaction conditions.

The reaction temperature is usually in the range of −30° C. to a boiling point of the reaction mixture. The reaction time is usually in the range of a moment to 72 hours.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 15

This is the production process according to the following scheme:

wherein Q, R¹, and R² are as defined above; G¹ is G-1 or G-2 as defined above; and X¹ is iodine, bromine, or chlorine.

1) Procedure for preparing compound [LXII] from compound [LXI]

Compound [LXII] can be prepared by reacting compound [LXI] with compound [LXIII] in the presence of a base in a solvent.

Amount of compound [LXIII]: 1 mole to an excessive amount for 1 mole of compound [LXI]

Solvent: ethers such as dioxane, alcohols such as ethanol, water, or the like

Temperature: 0° C. to heating temperature under reflux

Time: a moment to 48 hours

Base: alcoholates such as sodium ethoxide, organic bases such as triethylamine, or inorganic bases such as potassium carbonate

Amount of base: 2 moles to an excessive amount for 1 mole of compound [LXI]

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 16

This is the production process according to the following scheme:

wherein Q, X¹, R¹, R², E¹¹, and E¹² are as defined above; G² is G-3 as defined above; and R⁶⁰ hydrogen or C₁-C₅ alkyl.

1) Procedure for preparing compound [LXV] from compound [LXIV]

Compound [LXV] can be prepared by reacting compound [LIV] with compound [IXVl] or compound [LXVII] in a solvent and if necessary, in the presence of an acid.

Amount of compound [LXVI] or compound [LXVII]: 1 mole to an excessive amount for 1 mole of compound [LXIV]

Solvent: ethers such as dioxane, alcohols such as ethanol, organic acids such as acetic acid, water, or the like

Temperature: 0° C. to heating temperature under reflux

Time: a moment to 168 hours

Acid: inorganic acids such as hydrochloric acid

Amount of acid: a catalytic amount to an excessive amount

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

The following are production processes for intermediates or starting compounds used in the production of the present compounds.

In the aniline derivatives of the general formula:

wherein Q, G, and R³ are as defined above, which are the starting compounds in the production of the present compounds, the compounds of the general formula:

wherein Q and G¹ are as defined above, can be prepared, for example, by the following production process 17 or 18, and the compounds of the general formula:

wherein Q and G² are as defined above, can be prepared, for example, by the following production process 19.

Production Process 17

This is the production process in which a carbamate derivative of the general formula:

wherein Q is as defined above and R⁴⁶ is C₁-C₆ alkyl, is reacted with an amine derivative of the general formula:

H₂N—G¹—NH₂

wherein G¹ is as defined above.

The reaction is usually effected without any solvent or in a solvent. The reaction temperature is usually in the range of 20° C. to 200° C. The reaction time is usually in the range of a moment to 24 hours.

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the amine derivative of the above general formula for 1 mole of the carbamate compound of the above general formula, although they may suitably be changed with the reaction conditions.

The solvent which can be used may include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol dimethyl ether; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as DMF; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof. The amine derivatives of the above general formula can also be used as the solvents.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

The carbamate derivatives of the above general formula can be prepared by the known methods, for example, by reacting an isothiocyanate of Q-NCS (wherein Q is as defined above) with R⁴⁶OH (wherein R⁴ is as defined above).

The isothiocyanate of Q-NCS (wherein Q is as defined above) is commercially available or can be prepared, for example, by the procedures as described in the “Jikken Kagaku Kohza” (Maruzen Kabushiki Kaisha), 4th ed., vol. 20, pp. 483-489.

Production Process 18

This is the production process in which an isothiocyanate derivative of Q-NCS (wherein Q is as defined above) is reacted with an amine derivative of the above general formula.

The reaction is usually effected without any solvent or in a solvent.

The reaction temperature is usually in the range of 20° C. to 200° C. The reaction time is usually in the range of a moment to 24 hours.

The amounts of reagents to be used in the reaction are stoichiometrically 1 mole of the amine derivative of the above general formula for 1 mole of the isothiocyanate derivative of Q-NCS, although they may suitably be changed with the reaction conditions.

The solvent which can be used may include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, THF, and ethylene glycol dimethyl ether; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as DMF; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; water; and mixtures thereof The amine derivatives of the above general formula can also be used as the solvents.

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

Production Process 19

This is the production process according to the following scheme:

wherein R⁴⁷ an R⁴⁸ are independently C₁-C₆ alkyl; and Q, E¹¹, E¹², and G² are as defined above (see J. Med. Chem., 1997, 40, 18-23).

1) Procedure for preparing compound [LVI] from compound [LIV]

Compound [LVI] can be prepared by reacting compound [LIV] with compound [LV] in the presence of an acid in a solvent.

Amount of compound [LV]: 1 mole to an excessive amount for 1 mole of compound [LIV]

Solvent: ethanol or the like

Temperature: 0° C. to heating temperature under reflux

Time: a moment to 24 hours

Acid: organic acids such as methanesulfonic acid

Amount of acid: a catalytic amount to an excessive amount

After completion of the reaction, the crystals precipitated, if necessary, by the addition of water, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [LVII] from compound [LVI]

Compound [LVII] can be prepared by reacting compound [LVI] in the presence of an acid in a solvent.

Solvent: water or the like

Temperature: 0° C. to heating temperature under reflux

Time: a moment to 24 hours

Acid: inorganic acids such as hydrochloric acid

Amount of acid: a catalytic amount to an excessive amount

After completion of the reaction, the crystals precipitated by the addition of water are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

The aniline derivatives of Q-NH2 (wherein Q is as defined above) are known in the art, for example, in the published specification of European Patent Application, EP-61741-A; and the specifications of U.S. Pat. No. 4,770,695, No. 4,709,049, and No. 4,720,297, or can be prepared by the procedures as described therein.

Production Process 20

The 2-aminopyrimidine derivatives used in the production processes 15 and 16 can be prepared by the following scheme:

wherein Q, R¹, R², and R³³ are as defined above (see the published specification of European Patent Application EP-0396250).

1) Procedure for preparing compound [LXXI] from isothiocyanate derivative

Compound [LXXI] can be prepared by reacting compound [LXX] with an isothiocyanate derivative in the presence of a base in a solvent.

Amount of compound [LXX]: 1 mole to an excessive amount for 1 mole of isothiocyanate derivative

Solvent: N,N-dimethylformamide or the like

Temperature: 0° C. to 100° C.

Time: a moment to 24 hours

Base: inorganic bases such as sodium hydride

Amount of base: 1 mole to an excessive amount for 1 mole of isothiocyanate derivative

After completion of the reaction, the crystals precipitated, if necessary, by the addition of aqueous hydrochloric acid, are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

2) Procedure for preparing compound [LXXII] from compound Compound [LXII] can be prepared by methylating compound [LXXI] in the presence of a base in a solvent.

Amount of methylating agent: 1 mole to an excessive amount for 1 mole of compound [LXXI]

Methylating agent: iodomethane, dimethyl sulfate, or the like

Solvent: N,N-dimethylformamide or the like

Temperature: −10° C. to 100° C.

Time: a moment to 24 hours

Base: organic bases such as triethylamine, or inorganic bases such as potassium carbonate

Amount of base: 1 mole to an excessive amount for 1 mole of compound [LXXI]

After completion of the reaction, the crystals precipitated by the addition of water are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

3) Procedure for preparing compound [LXXIII] from compound [LXXII]

Compound [XIII] can be prepared by oxidizing compound [LXXII] in a solvent.

Amount of oxidizing agent: 2 moles to an excessive amount for 1 mole of compound [LXXII]

Oxidizing agent: m-chloroperbenzoic acid or the like

Solvent: chloroform or the like

Temperature: −10° C. to refluxing temperature

Time: a moment to 48 hours

After completion of the reaction, the reaction mixture is washed with an aqueous solution of sodium hydrogensulfite or the like and then subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

4) Procedure for preparing compound [LXXIV] from compound [LXXIII]

Compound [LXXIX] can be prepared by reacting compound [LXXIII] with ammonia in a solvent.

Amount of ammonia: 1 mole to an excessive amount for 1 mole of compound [LXXIII]

Solvent: 2-propanol, 2-methyl-2-propanol, or the like

Temperature: −10° C. to refluxing temperature

Time: a moment to 48 hours

After completion of the reaction, the reaction mixture is poured into water and the precipitated crystals are collected by filtration, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration. If necessary, purification may be carried out by an ordinary technique such as chromatography or recrystallization. Thus the desired compound can be isolated.

The presence compounds have excellent herbicidal activity and some of them exhibit excellent selectivity between crops and weeds. More particularly, the present compounds have herbicidal activity against various weeds which may cause some trouble in the foliar treatment and soil treatment on upland fields, such as listed below.

Polygonaceous weeds:

wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), Pennsylvania smartweed (Polygonum pensylvanicum), ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)

Portulacaceous weeds:

common purslane (Portulaca oleracea)

Caryophyllaceous weeds:

common chickweed (Stellaria media)

Chenopodiaceous weeds:

common lambsquarters (Chenopodium album), kochia (Kochia scoparia)

Amaranthaceous weeds:

redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthus hybridus)

Cruciferous (brassicaceous) weeds:

wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis), shepherdpurse (Capsella bursa-pastoris)

Leguminous (fabaceous) weeds:

hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia),

Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens)

Malvaceous weeds:

velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)

Violaceous weeds:

field pansy (Viola arvensis), wild pansy (Viola tricolor)

Rubiaceous weeds:

catchweed bedstraw (cleavers) (Galium aparine)

Convolvulaceous weeds:

ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis)

Labiate weeds:

red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)

Solanaceous weeds:

jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)

Scrophulariaceous weeds:

birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronica hederaefolia)

Composite weeds:

common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata or inodora), corn marigold (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort (Artemisia princeps), tall goldenrod (Solidago altissima)

Boraginaceous weeds:

forget-me-not (Myosotis arvensis)

Asclepiadaceous weeds:

common milkweed (Asclepias syriaca)

Euphorbiaceous weeds:

sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)

Graminaceous weeds:

barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis), goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), wild oats (Avena fatua), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicum dichotomifiorum), Texas panicum (Panicum texanum), shattercane (Sorghum vulgare)

Commelinaceous weeds:

common dayflower (Commelina communis)

Equisetaceous weeds:

field horsetail (Equisetum arvense)

Cyperaceous weeds:

rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus)

Furthermore, some of the present compounds exhibit no significant phytotoxicity on the main crops such as corn (Zea mays), wheat (Triticum aestivum), barley (Hordeum vulgare), rice (Oryza saliva), sorghum (Sorghum bicoloz), soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthus annuus), and canola (Brassica napus); horticultural crops such as flowers and ornamental plants; and vegetable crops.

The present compounds can also attain the effective control of various weeds which may cause some trouble in the no-tillage cultivation of soybean (Glycine max), corn (Zea mays), wheat (liticum aestivum), and other crops. Furthermore, some of them exhibit no significant phytotoxicity on the crops.

The present compounds also have herbicidal activity against various weeds which may cause some trouble in the flooding treatment on paddy fields, such as listed below.

Graminaceous weeds:

barnyardgrass (Echinochloa oryzicola)

Scrophulariaceous weeds:

common falsepimpernel (Lindernia procumbens)

Lythraceous weeds:

Indian toothcup (Rotala indica), red stem (Ammannia multiflora)

Elatinaceous weeds:

waterwort (Elatine triandra)

Cyperaceous weeds:

smallflower umbrella sedge (Cyperus dfformis), hardstem bulrush (Scirpus juncoides), needle spikerush (Eleocharis acicularis), water nutgrass (Cyperus serotinus), water chestnut (Eleocharis kuroguwai)

Pontederiaceous weeds:

monochoria (Monochoria vaginalis)

Alismataceous weeds:

arrowhead (Sagittaria pygmaea), arrowhead (Sagittaria trifolia),

waterplantain (Alisma canaliculatum)

Potamogetonaceous weeds:

roundleaf pondweed (Potamogeton distinctus)

Umbelloferous weeds:

watercelery sp. (Oenanthe javanica)

Furthermore, some of the present compounds exhibit no significant phytotoxicity on transplanted paddy rice.

The present compounds can also attain the control of a wide variety of weeds which grow or will grow in the orchards, grasslands, lawns, forests, waterways, canals, or other non-cultivated lands.

The present compounds also have herbicidal activity against various aquatic weeds, such as water hyacinth (Eichhornia crassipes), which grow or will grow at the waterside such as waterways or canals.

The present compounds have substantially the same characteristics as those of the herbicidal compounds disclosed in the published specification of International Patent Application, WO95/34659. In the case where crops with tolerance imparted by introducing a herbicide tolerance gene described in the published specification are cultivated, the present compounds can be used at larger rates than those used when ordinary crops without tolerance are cultivated, which makes it possible to control other unfavorable weeds more effectively.

When the present compounds are used as the active ingredients of herbicides, they are usually mixed with solid or liquid carriers or diluents, surfactants, and other auxiliary agents to give emulsifiable concentrates, wettable powders, flowables, granules, concentrated emulsions, water-dispersible granules, or other formulations.

These formulations may contain any of the present compounds as an active ingredient at an amount of 0.001 to 80% by weight, preferably 0.005 to 70% by weight, based on the total weight of the formulation.

The solid carrier or diluent which can be used may include, for example, fine powders or granules of the following materials: mineral matters such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, and calcite; organic substances such as walnut shell powder; water-soluble organic substances such as urea; inorganic salts such as ammonium sulfate; and synthetic hydrated silicon oxide. The liquid carrier or diluent which can be used may include, for example, aromatic hydrocarbons such as methylnaphthalene, phenylxylylethane, and alkylbenzene (e.g., xylene); alcohols'such as isopropanol, ethylene glycol, and 2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketones such as acetone, cyclohexanone, and isophorone; mineral oils such as machine oil; vegetable oils such as soybean oil and cottonseed oil; dimethylsulfoxide, N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, and water.

The surfactant used for emulsification, dispersing, or spreading may include surfactants of the anionic type, such as alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl aryl ethers; and surfactants of the nonionic type, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.

The auxiliary agent may include lignin sulfonates, alginates, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), and PAP (isopropyl acid phosphate).

The present compounds are usually formulated as described above and then used for pre- or post-emergence soil, foliar, or flooding treatment of weeds. The soil treatment may include soil surface treatment and soil incorporation. The foliar treatment may include application over the plants and directed application in which a chemical is applied only to weeds so as to keep off the crop plants.

The present compounds may often exhibit the enhancement of herbicidal activity when used in admixture with other herbicides. They can also be used in admixture with insecticides, acaricides, nematocides, fungicides, bactericides, plant growth regulators, fertilizers, and soil conditioners. Examples of the herbicide which can be used in admixture with the present compounds are atrazine, cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn, chlorotoluron, diuron, dymron, fluometuron, isoproturon, linuron, methabenzthiazuron, bromoxynil, ioxynil, ethalfluralin, pendimethalin, trifluralin, acifluorfen, acifluorfen-sodium, bifenox, chlomethoxynil, fomesafen, lactofen, oxadiazon, oxadiargyl, oxyfluorfen, carfentrazone, flumiclorac-pentyl, flumioxazine, fluthiacet-methyl, sulfentrazone, thidiazimin, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, DCPA, MCPA, MCPB, clomeprop, clopyralid, dicamba, dithiopyr, fluroxypyr, mecoprop, naproanilide, phenothiol, quinclorac, triclopyr, acetochlor, alachlor, butachlor, diethatyl-ethyl, metolachlor, pretilachlor, propachlor, bensulfuron-methyl, chlorsulfuron, chlorimuron-ethyl, halosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, sulfometuron-ethyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, azimsulfuron, cloransulam-methyl, cyclosulfamuron, flumetsulam, flupyrsulfuron, flazasulfuron, imazosulfuron, metosulam, prosulfuron, rimsulfuron, triflusulfuron-methyl, imazamethabenz-methyl, imazapyr, imazaquin, imazethapyr, imazameth, imazamox, bispyribac-sodium, pyriminobac-methyl, pyrithiobac-sodium, alloxydim-sodium, clethodim, sethoxydim, tralkoxydim, dichlofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl, cyhalofop-butyl, clodinafoppropargyl, benzofenap, clomazone, diflufenican, norflurazon, pyrazolate, pyrazoxyfen, isoxaflutole, sulcotrione, glufosinate-ammonium, glyphosate, bentazon, benthiocarb, bromobutide, butamifos, butylate, dimepiperate, dimethenamid, DSMA, EPTC, esprocarb, isoxaben, mefenacet, molinate, MSMA, piperophos, pyributicarb, propanil, pyridate, triallate, cafenstrol, flupoxam, and fluthiamide.

These compounds are described in the catalog of Farm Chemicals Handbook, 1995 (published by Meister Publishing Company); AG CHEM NEW COMPOUND REVIEW, VOL. 13, 1995 (published by AG CHEM INFORMATION SERVICES); and “Josouzai Kenkyu Souran” (published by Hakuyu-sha).

When the present compounds are used as the active ingredients of herbicides, the application amount, although it may vary with the weather conditions, formulation types, application times, application methods, soil conditions, crops to be protected, weeds to be controlled, and other factors, is usually in the range of 0.01 to 10,000 g, preferably 1 to 8000 g, per hectare. In the case of emulsifiable concentrates, wettable powders, flowables, concentrated emulsions, water-dispersible granules, or other similar formulations, they are usually applied after diluted in their prescribed amounts with water (if necessary, containing an adjuvant such as a spreading agent) at a ratio of 10 to 1000 liters per hectare. In the case of granules or some types of flowables, they are usually applied as such without any dilution.

The adjuvant which can be used herein, if necessary, may include, in addition to the surfactants as described above, polyoxyethylene resin acids (esters), lignin sulfonates, abietates, dinaphthylmethanedisulfonates, crop oil concentrates, and vegetable oils such as soybean oil, corn oil, cottonseed oil, and sunflower oil.

The present compounds can also be used as the active ingredients of harvesting aids such as defoliants and desiccants for cotton (Gossipyum spp.), and desiccants for potato (Solanum tuberosum). In these cases, the present compounds are usually formulated in the same manner as the case where they are used as the active ingredients of herbicides, and used alone or in admixture with other harvesting aids for foliar treatment before the harvesting of crops.

EXAMPLES

The present invention will be further illustrated by the following production examples, formulation examples, and test examples; however, the present invention is not limited to these examples.

Production Example 1

(Production of Present Compound 1-2)

First, 6.0 g of ethanol was added to 3.0 g of compound [1a], which was heated under reflux for 5.5 hours. The reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration. The crystals were washed with ethanol and then with hexane to give 2.2 g of compound [1b] (m.p., 93.9° C.).

Then, 1.9 g of ethylenediamine was added to 2.2 g of compound [1b], which was heated under reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were collected by filtration. The crystals were washed with water and recrystallized from a mixed solvent of ethanol and water (1:1) to give 0.8 g of compound [1c] (m.p., 160.3° C.).

Finally, 2 ml of toluene and 0.6 g of ethyl 4,4,4-trifluoroacetoacetate were added to 0.40 g of compound [1c], which was heated under reflux for 5.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 0.43 g of compound [1d] (present compound 1-2).

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 3.88-3.97 (2H, m), 4.08-4.16 (2H, m), 5.90 (1H, s), 7.21-7.27 (2H, m), 7.44-7.50 (2H, m)

Production Example 2

(Production of Present Compound 2-26)

First, 90 g of pyridine was added to 20 g of compound [2a], to which 28 g of triethylamine and 55 g of carbon disulfide were added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. Then, 17 g of methyl chloroformate was added dropwise under ice cooling, which was stirred at room temperature for 2 hours. The reaction mixture was made acidic by the addition of diluted hydrochloric acid, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated to give 24 g of compound [2b].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 2.32 (1H, t, J=2.7 Hz), 4.65 (2H, d, J=2.7 Hz), 4.66 (2H, s), 6.84 (1H, d, J=9.7 Hz), 7.00 (1H, d, J=7.0 Hz)

Then, 10 g of ethanol was added to 1.0 g of compound [2b], which was heated under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized by the addition of ethanol to give 1.1 g of compound [2c] (m.p., 189.3° C.).

Then, 0.65 g of ethylenediamine was added to 1.1 g of compound [2c], which was heated under reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were collected by filtration. The crystals were washed with 2-propanol and then with hexane to give 0.35 g of compound [2d] (m.p., 146.9° C.).

Finally, 10 ml of toluene and 3.4 g of ethyl 4,4,4-trifluoroacetoacetate were added to 1.7 g of compound [2d], which was heated under reflux for 5.0 hours. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 0.30 g of compound [2e] present compound 2-26).

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 2.29 (1H, t, J=2.4 Hz), 3.91-3.98 (2H, m), 4.08-4.19 (2H, m), 4.57 (1H, dd, J=2.4, 17.7 Hz), 4.65-4.67 (2H, m), 4.72 (1H, dd, J=2.4, 17.7 Hz), 5.90 (1H, s), 6.91 (1H, d, J=9.8 Hz), 7.11 (1H, d, J=6.8 Hz)

Production Example 3

(Production of Present Compounds 1-274 and 1-32)

First, 50 ml of toluene and 3.4 g of thiophosgene were added to 5 g of compound [3a], which was heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure to give compound [3b].

Then, 50 ml of ethanol was added to compound [3b], which was heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized by the addition of ethanol. The crystals were washed with hexane to give 2.8 g of compound [3c].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 1.37-1.47 (9H, m), 4.40-4.50 (1H, m), 4.60 (2H, q, J=6.9 Hz), 7.14 (1H, d, J=10.1 Hz), 7.90-8.25 (1H, br)

Then, 40 ml of toluene and 1.5 g of ethylenediamine were added to 2.7 g of compound [3c], which was heated under reflux for 7 hours. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were collected by filtration, and washed with water and then with hexane to give 2.2 g of compound [3d] (m.p., 162.8° C.).

Then, 30 ml of toluene and 3.2 ml of ethyl 4,4,4-trifluoroacetoacetate were added to 2.0 g of compound [3d]? which was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 0.80 g of compound [3e] (present compound 1-274) (m.p., 158.2° C.).

Then, 2 ml of concentrated sulfuric acid was added to 100 mg of compound [3e] under ice cooling, which was stirred for 10 minutes. The reaction mixture was returned to room temperature and then neutralized with aqueous sodium hydrogencarbonate solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, which afforded 75 mg of compound [3f] (present compound 1-32).

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 3.95-4.27 (4H, m), 5.96 (1H, s), 6.49 (1H, d, J=6.7 Hz), 7.20 (1H, d, J=9.0 Hz).

Production Example 4

(Production of Present Compound 1-406)

First, 1 ml of N,N-dimethylformamide, 40 mg of potassium carbonate, and 50 mg of ethyl bromoacetate were added to 75 mg of compound [3f], which was stirred at robm temperature for 2 hours. Then, water was added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with hexane, which afforded 70 mg of compound [4a] (present compound 1-406).

¹H-NMR (300 MHz, CDCl₃, TMS) δ ppm): 1.28 (3H, t, J=7.1 Hz), 3.88-3.97 (2H, m), 4.08-4.17 (2H, m), 4.25 (2H, q, J=7.1 Hz), 4.65 (2H, s), 5.87 (1H, s), 6.88 (1H, d, J=6.3 Hz), 7.32 (1H, d, J=8.8 Hz)

Production Example 5

(Production of Present Compound 1-460)

In the same manner as described in Production Example 4, except that ethyl 2-bromopropionate was substituted for ethyl bromoacetate, 0.10 g of compound [5a] (present compound 1-460) was obtained from 0.10 g of compound [31].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 1.19-1.29 (3H, m), 1.66 (3H, d, J=6.8 Hz), 3.87-3.97 (2H, m), 4.08-4.27 (4H, m), 4.62-4.72 (1H, m), 5.86 (1H, s), 6.83-6.93 (1H, m), 7.28-7.32 (1H, m)

Production Example 6

(Production of Present Compound 1-340)

In the same manner as described in Production Example 4, except that propargyl bromide was substituted for ethyl bromoacetate, 0.10 g of compound [6a] (present compound 1-340) was obtained from 0.10 g of compound [3f].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 2.56 (1H, t, J=2.3 Hz), 3.90-3.98 (2H, m), 4.08-4.18 (2H, m), 4.74 (2H, d, J=2.3 Hz), 5.88 (1H, s), 7.03 (1H, d, J=6.4 Hz), 7.31 (1H, d, J=9.1 Hz)

Production Example 7

(Production of Present Compound 1-346)

In the same manner as described in Production Example 4, except that 1-methyl-2-propynyl bromide was substituted for ethyl bromoacetate, 0.10 g of compound [7a] (present compound 1-346) (m.p., 137.6° C.) was obtained from 0.11 g of compound [3f].

Production Example 8

(Production of Present Compounds 1-454, 1-448, and 1-562)

In the same manner as described in Production Example 4, except that methyl 2-bromopropionate was substituted for ethyl bromoacetate, 2.7 g of compound [8a] (present compound 1-454) (m.p., 99.7° C.) was obtained from 2.5 g of compound [3f].

Then, 10 ml of 36% hydrochloric acid was added to 1.8 g of compound [8a], which was heated at 70° C. under stirring for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 1.6 g of compound [8b] (present compound 1-448) (m.p., 185.4° C.).

Then, 2 ml of dimethylsulfoxide, 2 ml of tetrahydrofuran, and 0.40 g of N,N-carbonyldiimidazole were added to 0.40 g of compound [8b], which was heated under stirring for 2 hours. Dimethylamine was blown into the reaction mixture. Then, the reaction mixture was subjected to silica gel column chromatography, which afforded 0.45 g of compound [8c] (present compound 1-562).

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 1.67 (3H, d, J=6.8 Hz), 2.91 (3H, s), 3.11 (3H, s), 3.87-3.99 (2H, m), 4.08-4.18 (2H, m), 4.86-4.98 (1H, m),5.85 (1H, s), 6.90 (0.6H, d, J=6.5 Hz), 6.93 (0.4H, d, J=6.6 Hz), 7.31 (1H, d,J=8.9 Hz)

Production Example 9

(Production of Present Compound 1-514)

In the same manner as described in Production Example 4, except that 2-chloro-N,N-diemthylacetamide was substituted for ethyl bromoacetate, 0.54 g of compound [9a] (present compound 1-514) was obtained from 0.50 g of compound [3f].

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 2.95 (3H, s), 3.12 (3H, s), 3.89-3.96 (2H, m), 4.07-4.16 (2H, m), 4.73 (2H, s), 5.86 (1H, s), 7.05 (1H, d, J=6.4 Hz), 7.30 (1H, d, J=8.8 Hz)

Production Example 10

(Production of Present Compound 1-262)

In the same manner as described in Production Example 4, except that methyl iodide was substituted for ethyl bromoacetate, 0.40 g of compound [lOa] (present compound 1-262) (m.p., 149.2° C.) was obtained from 0.51 g of compound [3f].

Production Example 11

(Production of Present Compound 1-268)

In the same manner as described in Production Example 4, except that ethyl bromide was substituted for ethyl bromoacetate, 0.44 g of compound [11a] (present compound 1-268) (m.p., 142.2° C.) was obtained from 0.51 g of compound [3f].

Production Example 12

(Production of Present Compound 1-280)

In the same manner as described in Production Example 4, except that propyl bromide was substituted for ethyl bromoacetate, 0.35 g of compound [12a] (present compound 1-280) (m.p., 171.0° C.) was obtained from 0.40 g of compound [3f].

Production Example 13

(Production of Present Compound 1-1246)

In the same manner as described in Production Example 4, except hat isobutyl bromide was substituted for ethyl bromoacetate, 0.15 g of compound [13a] (present compound 1-1246) was obtained from 0.50 g of compound [3f].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 1.02 (1H, s), 1.04 (1H, s), 2.03-2.22 (1H, m), 3.73 (2H, d, J=6.5 Hz), 3.90-4.01 (2H, m), 4.09-4.18 (2H, m), 5.88 (1H, s), 6.81 (1H, d, J=6.4 Hz), 7.29 (1H, d, J=9.0 Hz)

Production Example 14

(Production of Present Compound 1-310)

In the same manner as described in Production Example 4, except that allyl bromide was substituted for ethyl bromoacetate, 0.46 g of compound [14a] (present compound 1-310) (m.p., 146.6° C.) was obtained from 0.50 g of compound [3f].

Production Example 15

(Production of Present Compound 1-370)

In the same manner as described in Production Example 4, except that bromoacetonitrile was substituted for ethyl bromoacetate, 0.13 g of compound [15a] (present compound 1-370) was obtained from 0.50 g of compound [3f].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 3.89-3.98 (2H, m), 4.09-4.19 (2H, m), 4.79 (2H, s), 5.88 (1H, s), 7.09 (1H, d, J=6.2 Hz), 7.35 (1H, d, J=8.8 Hz)

Production Example 16

(Production of Present Compounds 1-5, 1-14, and 1-23)

First, 27.2 g of compound [16a] was dissolved in 300 ml of toluene, to which 23.6 g of thiophosgene was added. The reaction mixture was heated under reflux for 3 hours and then concentrated to give 2-chloro-4-fluorophenylisothiocyanate. Then, 100 ml of ethanol was added to the 2-chloro-4-fluorophenylisothiocyanate. The reaction mixture was heated under reflux for 3 hours and then concentrated to give 37.5 g of compound [16b] (m.p., 87.9° C).

Then, 37 g of compound [16b] was dissolved in 50 ml of toluene, to which 14.3 g of ethylenediamine was added. The reaction mixture was heated under reflux for 2.5 hours and then poured into water, which was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and then concentrated. The precipitated crystals were washed with a mixed solution of hexane and diethyl ether (1:1) to give 28 g of compound [16c] (m.p., 127.8° C.).

Then, 27 g of compound [16c] and 25.6 g of ethyl 4,4,4-trifluoroacetoacetate were heated under reflux in 140 ml of toluene for 2.5 hours. The reaction mixture was concentrated, and the residue was subjected to silica gel chromatography (eluent, hexane : ethyl acetate=2:1), which afforded 10.3 g of compound [16d] (present compound 1-5) (m.p., 112.6° C.).

Then, 8.4 g of compound [16d] was dissolved in 30 ml of concentrated sulfuric acid, followed by ice cooling, to which a mixed acid of 1.7 g of fuming nitric acid and 1.5 ml of concentrated sulfuric acid was added dropwise at 0° C. to 5° C. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour and then poured onto ice, which was neutralized with saturated aqueous sodium hydrogencarbonate solution, while keeping the reaction mixture below 10° C. The precipitated crystals were collected by filtration, washed with water, and dried, which afforded 7.6 g of compound [16e] (present compound 1-14) (m.p., 178.1° C.).

Then, 3.3 g of iron powder, and a mixed solution of 6 ml of acetic acid and 12 ml of water were stirred at 25° C. for 30 minutes. While keeping the reaction mixture below 35° C., a solution of 3.3 g of compound [16e] in 40 ml of ethyl acetate was added dropwise to the reaction mixture. After completion of the addition, stirring was continued for a while. The reaction mixture was poured into water, which was then extracted with ethyl acetate. The organic layer was washed with water, neutralized, dried, and concentrated. The residue was subjected to silica gel chromatography (eluent, hexane:ethyl acetate=1:2), which afforded 1.05 g of compound [16f] (present compound 1-23).

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 3.90-4.17 (6H, m), 5.87 (1H, s), 6.68 (1H, d, J=6.6 Hz), 7.19 (1H, d, J=9.0 Hz)

Production Example 17

(Production of Present Compound 1-88)

First, 0.25 g of compound [16f] was dissolved in 3 g of pyridine, to which 0.1 g of methanesulfonyl chloride was added. The reaction mixture was stirred for 4 hours and then poured into water, which was extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. The precipitated crystals were washed with isopropanol, which afforded 0.15 g of compound [17a] (present compound 1-88) (m.p., 259.8° C.; decomposition).

Production Example 18

(Production of Present Compound 1-220)

First, 2.0 g of ethyl 2-bromopropionate was added to 0.3 g of compound [16f], which was heated at 130° C. for 3 hours. Excessive ethyl 2-bromopropionate was removed by distillation, and the residue was dissolved in ethyl acetate, which was washed with aqueous sodium hydrogencarbonate. The organic layer was dried and concentrated, and the precipitated crystals were washed with a mixed solvent of hexane and diethyl ether (1:2), which afforded 0.14 g of compound [18a] (present compound 1-220) (m.p., 99.1° C.).

Production example 19

(Present Compound 1-1096)

First, a solution of 0.2 g of compound [16f] in 10 ml of acetonitrile was added dropwise to a solution of 1.5 g of methyl acrylate, 0.1 g of amyl nitrite, and 0.08 g of copper(II) chloride at room temperature. After completion of the addition, the reaction mixture was stirred for 10 hours and then poured into water, which was extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated, and the residue was subjected to silica gel column chromatography (eluent, hexane: ethyl acetate=3:1), which afforded 0.2 g of compound [19a] (present compound 1-1096).

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 3.22-3.49 (2H, m), 3.73 (1.5H, s), 3.76 (1.5H, s), 3.89-3.98 (2H, m), 4.10-4.16 (2H, m), 4.50-4.57 (1H, m), 5.85 (0.5H, s), 5.87 (0.5H, s), 7.24-7.46 (2H, m)

Production Example 20

(Production of Present Compound 1-712)

First, 7.1 g of compound [20a] was suspended in 50 ml of toluene, to which 3.9 g of thiophosgene was added. The reaction mixture was heated under reflux for 3 hours and then concentrated. Then, 50 ml of ethanol was added to the residue. The reaction mixture was heated under reflux for another 3 hours and then concentrated. The precipitated crystals were washed with a mixed solvent of hexane and diethyl ether (1:1) to give 10.1 g of compound [20b].

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 1.25 (3H, t, J=7.1 Hz), 1.43 (3H, t, J=7.1 Hz), 3.66 (2H, s), 4.18 (2H, q, J=7.1 Hz), 4.62 (2H, q, J=7.1 Hz), 7.20 (1H, d, J=10.1 Hz), 7.80-8.38 (1H, br) Then, 10.1 g of compound [20b] was dissolved in 100 ml of toluene, to which 1.9 g of ethylenediamine was added at room temperature. The reaction mixture was stirred for 30 minutes, heated under reflux for 2 hours and then concentrated. The precipitated crystals were washed with diethyl ether to give 5.9 g of compound [20c].

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 1.24 (3H, t, J=7.2 Hz), 3.56 (2H, s), 3.57 (4H, s), 4.14 (2H, q, J=7.2 Hz), 7.12 (1H, d, J=10.1 Hz), 7.21 (1H, d, J=8.6 Hz)

A solution of 5.9 g of compound [20c] and 3.3 g of ethyl 4,4,4-trifluoroacetoacetate in 20 ml of toluene was heated under reflux for 6 hours. The reaction mixture was concentrated, and the residue was subjected to silica gel chromatography (eluent, hexane: ethyl acetate=1:1), which afforded 2.9 g of compound [20d] (present compound 1-712). ¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 1.23 (3H, t, J=7.1 Hz), 3.64 (2H, s), 3.89-3.96 (2H, m), 4.10-4.20 (4H, m), 5.87 (1H, s), 7.34 (1H, d, J=9.1 Hz), 7.47 (1H, d, J=7.3 Hz)

Production Example 21

(Production of Present Compounds 1-1255 and 1-1257)

First, 10.4 g of sodium borohydride was added to a solution of 101 g of compound [21a] in 700 ml of methanol under ice cooling. The reaction mixture was stirred at room temperature for 30 minutes, into which diluted hydrochloric acid was poured. The precipitated crystals were collected by filtration to give 140 g of crude compound [21b].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 4.86 (2H, s), 7.52 (1H, d, J=8.7 Hz), 8.09 (1H, dd, J=2.8, 8.7 Hz), 8.45 (1H, d, J=2.8 Hz)

A mixture of 1000 ml of water, 100 ml of acetic acid, and 158 g of iron was heated to 60° C., to which a solution of 140 g of crude compound [21b] in 60 ml of ethyl acetate was added dropwise. The reaction mixture was stirred until it came to room temperature, and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated to give 59 g of compound [21c].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 3.73 (2H, br), 4.67 (2H, s), 6.53 (1H, dd, J=2.8, 8.4 Hz), 6.83 (1H, d, J=2.8 Hz), 7.09 (1H, d, J=8.4 Hz) Then, 5.6 ml of thiophosgene was added dropwise to a solution of 10.6 g of compound [21c] in 100 ml of toluene. The reaction mixture was heated under reflux for 1 hour and then concentrated to give 12 g of crude compound [21d].

¹H-NMR (250 MHz, CDCl₃, TMS) t (ppm): 2.00 (1H, t, J=6.0 Hz), 4.76 (2H, d, J=6.0 Hz), 7.08 (1H, dd, J=2.5, 8.5 Hz), 7.32 (1H, d, J=8.5 Hz), 7.42 (1H, d, J=2.5 Hz)

Then, 50 ml of ethanol was added to 12 g of crude compound [21d]. The reaction mixture was heated under reflux for 1 hour and then concentrated. The residue was subjected to silica gel column chromatography, which afforded 2.6 g of compound [21e].

Then, 100 ml of toluene and 1.7 ml of ethylenediamine were added to 2.3 g of compound [21e]. The reaction mixture was heated under reflux for 5 hours and then poured into water, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated to give 1.3 g of crude compound [21f]

Then, 10 ml of toluene and 1.6 g of ethyl 3-methoxy-4,4,4-trifluorochrotonate were added to 1.3 g of crude compound [21f]. The reaction mixture was heated under reflux for 8.5 hours and then concentrated to give a crude compound [21g]. This crude product was subjected to silica gel column chromatography, which afforded 0.12 g of compound [21g] (present compound 1-1255) (m.p., 184.3° C.).

Then, 2 ml of anhydrous acetic acid and 2 ml of pyridine were added 180 mg of crude compound [21g], and the reaction was allowed to proceed at room temperature overnight. The reaction mixture was poured into water, which was then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 20 mg of compound [21h] (present compound 1-1257).

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 2.13 (3H, s), 3.89-3.96 (2H, m), 4.09-4.16 (2H, m), 5.22 (2H, s), 5.90 (1H, s), 7.21 (1H, dd, J=2.5, 8.5 Hz), 7.39 (1H, d, J=2.5 Hz), 7.52 (1H, d, J=8.5 Hz)

Production Example 22

(Production of Present Compound 6-2)

First, 12.0 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added to a suspension of 2.6 g of sodium hydride in 50 ml of N,N-dimethylformamide, while keeping the reaction mixture below 10° C. The reaction mixture was then stirred at room temperature for 30 minutes, to which a solution of 10.0 g of compound [1a] in 30 ml of toluene was added dropwise, while keeping the reaction mixture below 40° C. After completion of the addition, the reaction mixture was stirred at room temperature for 2 hours and then poured into water, which was neutralized with diluted hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated. The crystals thus obtained were washed with a mixed solvent of hexane and diethyl ether (1:1) to give 11.3 g of compound [22b].

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 6.43 (1H, s), 7.12-7.15 (2H, m), 7.49-7.51 (2H, m), 9.38-10.2 (1H, br)

Then, 4.0 g of triethylamine was added to a solution of 10.0 g of compound [22b] in 50 ml of N,N-dimethylformamide, followed by stirring for 30 minutes and addition of 5.6 g of iodomethane. The reaction mixture was stirred for 1 hour and then poured into water, which was neutralized with diluted hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated to give 9.8 g of compound [22c] (m.p., 109.7° C.).

Then, 13 g of m-chloroperbenzoic acid was added to a solution of 6.0 g of compound [22c] in 40 ml of chloroform. The reaction mixture was stirred for 12 hours and then filtered. The filtrate was washed with aqueous sodium thiosulfate solution and then with aqueous potassium carbonate solution, dried over magnesium sulfate, and then concentrated to give 5.8 g of compound [22d].

¹H-NMR (250 MHz, CDCl₃, TMS)δ (ppm): 3.38 (3H, s), 7.04 (1H, s), 7.26-7.30 (2H, m), 7.51-7.55 (2H, m) Then, 3.5 g of compound [22d] was suspended in 20 ml of 2-methyl-2-propanol, into which ammonia gas was blown for 30 minutes, and the reaction mixture was poured into water. The precipitated crystals were collected by filtration, washed with water, and then dried to give 1.4 g of compound [22e] (m.p., 214.3° C.).

Then, 0.5 g of 2-bromo-1,1-diethoxyethane was added to a mixed solution of 1.0 g of concentrated hydrochloric acid and 2.0 g of acetic acid, followed by stirring at room temperature for 15 minutes and addition of 0.5 g of compound [22e]. The reaction mixture was heated under reflux for 10 hours and then poured into water, which was extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium hydrogen-carbonate solution, dried over magnesium sulfate, and then concentrated. The residue was subjected to silica gel chromatography (eluent, hexane ethyl acetate=4 1), which afforded 0.24 g of compound [22f] (present compound 6-2) (m.p., 221.4° C.).

Production Example 23

(Present Compounds 6-32 and 6-274)

First, 25.0 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added to a suspension of 5.4 g of sodium hydride in 100 ml of N,N-dimethylformamide, while keeping the reaction mixture below 10° C. The reaction mixture was then stirred at room temperature for 30 minutes, to which a solution of 30.0 g of compound [3b] in 150 ml of toluene was added dropwise, while keeping the reaction mixture below 40° C. After completion of the addition, the reaction mixture was stirred at room temperature for 2 hours and then poured into water, which was neutralized with diluted hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated. The crystals thus obtained were washed with a mixed solvent of hexane and diethyl ether (1 : 1) to give 16.0 g of compound [23a] (m.p., 224.9° C.).

Then, 5.0 g of triethylamine was added to a solution of 16.0 g of compound [23a] in 100 ml of N,N-dimethylformamide, followed by stirring for 30 minutes and addition of 6.0 g of iodomethane. The reaction mixture was stirred for another 1 hour and then poured into water, which was neutralized with diluted hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated to give 16.4 g of compound [23b] (m.p., 88.4° C.).

Then, 28.6 g of m-chloroperbenzoic acid was added to a solution of 16.0 g of compound [23b] in 150 ml of chloroform. The reaction mixture was stirred for 12 hours and then filtered. The filtrate was washed with aqueous sodium thiosulfate solution and then with aqueous potassium carbonate solution, dried over magnesium sulfate, and then concentrated to give 16.5 g of compound [23c] (m.p., 164.8° C.).

Then, 16.2 g of compound [23c] was suspended in 150 ml of 2-methyl-2-propanol, into which ammonia gas was blown for 30 minutes, and the reaction mixture was poured into water. The precipitated crystals were collected by filtration, washed with water, and then dried to give 11.2 g of compound [23d] (m.p., 260.4° C.).

Then, 13.0 g of 2-bromo-1,1-dimethoxyethane was added to a mixed solution of 5.0 g of concentrated hydrochloric acid and 26.0 g of acetic acid, followed by stirring at room temperature for 15 minutes and addition of 11.0 g of compound [23d]. The reaction mixture was heated under reflux for 10 hours and then poured into water, which was extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate, and then concentrated. The residue was subjected to silica gel chromatography (eluent, hexane ethyl acetate=5:1), which afforded 6.7 g of compound [23e] (present compound 6-32) (m.p., 132.1° C.).

Finally, 6.0 g of compound [23e] was added to 50 ml of concentrated sulfuric acid. The reaction mixture was stirred for 3 hours and then poured into ice water, which was stirred for another 1 hour and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated. The residue was subjected to silica gel chromatography (eluent, hexane:ethyl acetate=3:1), which afforded 2.4 g of compound [23f] (present compound 6-274).

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 6.73 (1H, s), 6.74 (1H, d, J=6.5 Hz), 7.19 (1H, d, J=1.9 Hz), 7.29 (1H, d, J=1.9 Hz), 7.32 (1H, d, J=9.0 Hz)

Production Example 24

(Production of Present Compounds 16-32 and 16-274)

First, 18.4 g of ethyl 3-amino-4-chloro-4,4-difluorochlotonate was added to a suspension of 3.6 g of sodium hydride in 50 ml of N,N-dimethylformamide, while keeping the reaction mixture below 10° C. The reaction mixture was stirred at room temperature for 30 minutes, to which a solution of 20.0 g of compound [3b] in 100 ml of toluene was added dropwise, while keeping the reaction mixture below 40° C. After completion of the addition, the reaction mixture was stirred at room temperature for 2 hours and then poured into water, which was neutralized with diluted hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated. The crystals thus obtained were washed with a mixed solvent of hexane and diethyl ether (1:1) to give 8.2 g of compound [24a] (m.p., 213.7° C.).

Then, 2.5 g of triethylamine was added to a solution of 8.2 g of compound [24a] in 50 ml of N,N-dimethylformamide, followed by stirring for 30 minutes and addition of 4.4 g of iodomethane. The reaction mixture was stirred for 1 hour and then poured into water, which was neutralized with diluted hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated to give 8.3 g of compound [24b] (m.p., 109.3° C.).

Then, 14.0 g of m-chloroperbenzoic acid was added to a solution of 8.2 g of compound [24b] in 100 ml of chloroform. The reaction mixture was stirred for 18 hours and then filtered. The filtrate was washed with aqueous sodium thiosulfate solution and then with aqueous potassium carbonate solution, dried over magnesium sulfate, and then concentrated to give 8.1 g of compound [24c] (m.p., 131.4° C.).

Then, 8.2 g of compound [24c] was suspended in 75 ml of 2-methyl-2-propanol, into which ammonia gas was blown for 30 minutes, and the reaction mixture was poured into water. The precipitated crystals were collected by filtration, washed with water, and then dried to give 5.4 g of compound [24d] (m.p., 261.3° C.).

Then, 6.0 g of 2-bromo-1,1-dimethoxyethane was added to a mixed solution of 3.0 g of concentrated hydrochloric acid and 12.0 g of acetic acid, followed by stirring at room temperature for 15 minutes and addition of 5.4 g of compound [24d]. The reaction mixture was heated under reflux for 14 hours and then poured into water, which was extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate, and then concentrated. The residue was subjected to silica gel chromatography (eluent, hexane ethyl acetate=5:1), which afforded 2.9 g of compound [24e] (present compound 16-32) (m.p., 112.6° C.).

Finally, 2.5 g of compound [24e] was added to 50 ml of concentrated sulfuric acid. The reaction mixture was stirred for 2 hours and then poured into ice water, which was stirred for another 1 hour and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and then concentrated, which afforded 1.4 g of compound [24f] (present compound 16-274).

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 6.68 (1H, s), 6.75 (1H, d, J=6.5 Hz), 7.20 (1H, d, J=1.9 Hz), 7.32 (1H, d, J=9.0 Hz), 7.38 (1H, d, J=1.9 Hz)

Production Example 25

(Production of Present Compound 11-2)

First, 2 ml of toluene and 1.0 g of ethyl 4-chloro-4,4-difluoro-3-methoxychrotonate were added to 1.0 g of compound [1c]. The reaction mixture was heated under reflux for 5 hours and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 0.4 g of compound [25] (Present Compound 11-2).

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 3.88-3.96 (2H, m), 4.15-4.24 (2H, m), 5.85 (1H, s), 7.20-7.27 (2H, m), 7.44-7.51 (2H, m)

Production Example 26

In the same manner as described in Production Example 25, except that 1.0 g of ethyl 4,4,5,5,5-pentafluoro-3-methoxy-3-methoxy-2-pentenate was substituted for 1.0 g of ethyl 4-chloro-4,4-difluoro-3-methoxychrotonate, 5 0.2 g of compound [26] was obtained.

¹H-NMR (250 MHz, CDCl₃, TMS) δ (ppm): 3.88 (2H, t, J=7.5 Hz), 4.11 (2H, t, J=7.5 Hz), 5.87 (1H, s), 7.24 (2H, d, J=7.5 Hz), 7.48 (2H, d, J=7.5 Hz)

Production Example 27

First, 50 ml of toluene and 2 ml of 1,2-diaminopropane were added to 1.5 g of compound [3c]. The reaction mixture was heated under reflux for 2 hours and then concentrated to give 1.8 g of crude compound [27a]. Then, 1.0 g of ethyl 4,4,4-trifluoro-3-methoxychrotonate and 10 ml of toluene were added to 1.8 g of crude product. The reaction mixture was heated under reflux for 6 hours and then concentrated. The residue was subjected to silica gel column chromatography, which afforded 0.40 g of 1:1 mixture of compounds [27b] and [27c].

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 1.19-1.31 (3H, m), 1.32-1.40 (6H, m), 3.60-3.70 (1H, m), 4.17-4.30 (2H, m), 4.38-4.49 (1H, m), 5.86 (0.5H, s), 5.87 (0.5H, s), 6.82-6.88 (1H, m), 7.27 (1H, d, J=9.0)

Production Example 28

First, 2.3 ml of N,N-dimethylformamide, 239 mg of potassium carbonate, and 154 mg of allyl bromide were added to 400 mg of compound [23f] (present compound 6-274), followed by stirring at room temperature for 1.5 hours. Then, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane : ethyl acetate=3:1), which afforded 366 mg of compound [28a] present compound 6-310) (m.p., 103.3° C.).

Production Example 29

First, 4.0 ml of N,N-dimethylformamide, 419 mg of potassium carbonate, and 201 mg of methallyl chloride were added to 700 mg of compound [23f] (present compound 6-274), followed by stirring at 60° C. for 4 hours. Then, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate 3:1), which afforded 490 mg of compound [29a] (present compound 6-334).

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 1.84 (3H, s), 4.45 (2H, s), 5.01 (1H, s), 5.13 (1H, s), 6.69 (1H, s), 6.95 (1H, d, J 6.2 Hz), 7.15 (1H, d, J=1.8 Hz), 7.26 (1H, d, J=1.8 Hz), 7.39 (1H, d, J=9.0 Hz)

Production Example 30

First, 4.6 ml of N,N-dimethylformamide, 478 mg of potassium carbonate, and 282 mg of 2-chloroallyl chloride were added to 800 mg of compound [23f] (present compound 6-274), followed by stirring at 60° C. for 3 hours. Then, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane: ethyl acetate=3:1), which afforded 551 mg of compound [32a] (present compound 6-316).

¹H-NMR (300 MHz, CDCl₃, TMS) δ (ppm): 4.60 (2H, s), 5.48 (1H, s), 5.66-5.67 (1H, m), 6.69 (1H, s), 6.98 (1H, d, J=6.2 Hz), 7.14 (1H, s), 7.26 (1H, s), 7.40 (1H, d, J=8.9 Hz)

Production Example 31

First, 12.5 ml of thiophosgene was added dropwise to a solution of 29 g of compound [33a] in 300 ml of toluene, which was heated under reflux for 2 hours. After completion of the reaction, the reaction mixture was concentrated to give 31 g of crude compound [33b].

Then, 50 ml of ethanol was added to 12 g of crude compound [33b], which was heated under reflux for 2 hours. After completion of the reaction, the reaction mixture was concentrated. The precipitated crystals were washed with hexane and then recrystallized from 2-propanol to give 6.1 g of compound [33c] (m.p., 83.8° C.).

Then, 1.7 ml of ethylenediamine was added to a solution of 6.1 g of compound [33c] in 60 ml of toluene, which was heated under reflux for 4 hours. After completion of the reaction, the reaction mixture was concentrated. The precipitated crystals were washed with 2-propanol to give 4.2 g of compound [33d] (m.p., 148.0° C.).

Finally, 2.0 g of compound [33d], 20 ml of toluene, and 1.6 g of ethyl 3-trifluoromethyl-3-methoxyacrylate were mixed and heated under reflux for 7.5 hours. After completion of the reaction, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated. The residue was subjected to column chromatography, which afforded 0.3 g of compound [33e].

Some examples of the present compounds are shown, together with their compound numbers, in Tables 1 to 248. In these tables, “n”, “i”, “s”, and “c” means “normal-”, “iso-”, “secondary-”, and “cyclo-”, respectively.

Compounds of the general formula:

TABLE 1 X Y R¹ B 1-1 H F H H 1-2 H Cl H H 1-3 H Br H H 1-4 F F H H 1-5 F Cl H H 1-6 F Br H H 1-7 Cl F H H 1-8 Cl Cl H H 1-9 Cl Br H H 1-10 H F H NO₂ 1-11 H Cl H NO₂ 1-12 H Br H NO₂ 1-13 F F H NO₂ 1-14 F Cl H NO₂ 1-15 F Br H NO₂ 1-16 Cl F H NO₂ 1-17 Cl Cl H NO₂ 1-18 Cl Br H NO₂ 1-19 H F H NH₂ 1-20 H Cl H NH₂ 1-21 H Br H NH₂ 1-22 F F H NH₂ 1-23 F Cl H NH₂ 1-24 F Br H NH₂ 1-25 Cl F H NH₂

TABLE 2 X Y R¹ B 1-26 Cl Cl H NH₂ 1-27 Cl Br H NH₂ 1-28 H F H OH 1-29 H Cl H OH 1-30 H Br H OH 1-31 F F H OH 1-32 F Cl H OH 1-33 F Br H OH 1-34 Cl F H OH 1-35 Cl Cl H OH 1-36 Cl Br H OH 1-37 H F H SH 1-38 H Cl H SH 1-39 H Br H SH 1-40 F F H SH 1-41 F Cl H SH 1-42 F Br H SH 1-43 Cl F H SH 1-44 Cl Cl H SH 1-45 Cl Br H SH 1-46 H F H SO₂Cl 1-47 H Cl H SO₂Cl 1-48 H Br H SO₂Cl 1-49 F F H SO₂Cl 1-50 F Cl H SO₂Cl

TABLE 3 X Y R¹ B 1-51 F Br H SO₂Cl 1-52 Cl F H SO₂Cl 1-53 Cl Cl H SO₂Cl 1-54 Cl Br H SO₂Cl 1-55 H F H NHCH₃ 1-56 H Cl H NHCH₃ 1-57 F F H NHCH₃ 1-58 F Cl H NHCH₃ 1-59 Cl F H NHCH₃ 1-60 Cl Cl H NHCH₃ 1-61 H F H NHC₂H₅ 1-62 H Cl H NHC₂H₅ 1-63 F F H NHC₂H₅ 1-64 F Cl H NHC₂H₅ 1-65 Cl F H NHC₂H₅ 1-66 Cl Cl H NHC₂H₅ 1-67 H F H NHCH₂CH═CH₂ 1-68 H Cl H NHCH₂CH═CH₂ 1-69 F F H NHCH₂CH═CH₂ 1-70 F Cl H NHCH₂CH═CH₂ 1-71 Cl F H NHCH₂CH═CH₂ 1-72 Cl Cl H NHCH₂CH═CH₂ 1-73 H F H NHCH₂C≡CH 1-74 H Cl H NHCH₂C≡CH 1-75 F F H NHCH₂C≡CH

TABLE 4 X Y R¹ B 1-76 F Cl H NHCH₂C≡CH 1-77 Cl F H NHCH₂C≡CH 1-78 Cl Cl H NHCH₂C≡CH 1-79 H F H NHCH(CH₃)C≡CH 1-80 H Cl H NHCH(CH₃)C≡CH 1-81 F F H NHCH(CH₃)C≡CH 1-82 F Cl H NHCH(CH₃)C≡CH 1-83 Cl F H NHCH(CH₃)C≡CH 1-84 Cl Cl H NHCH(CH₃)C≡CH 1-85 H F H NHSO₂CH₃ 1-86 H Cl H NHSO₂CH₃ 1-87 F F H NHSO₂CH₃ 1-88 F Cl H NHSO₂CH₃ 1-89 Cl F H NHSO₂CH₃ 1-90 Cl Cl H NHSO₂CH₃ 1-91 H F H NHSO₂C₂H₅ 1-92 H Cl H NHSO₂C₂H₅ 1-93 F F H NHSO₂C₂H₅ 1-94 F Cl H NHSO₂C₂H₅ 1-95 Cl F H NHSO₂C₂H₅ 1-96 Cl Cl H NHSO₂C₂H₅ 1-97 H F H NHSO₂CH₂Cl 1-98 H Cl H NHSO₂CH₂Cl 1-99 F F H NHSO₂CH₂Cl 1-100 F Cl H NHSO₂CH₂Cl

TABLE 5 X Y R¹ B 1-101 Cl F H NHSO₂CH₂Cl 1-102 Cl Cl H NHSO₂CH₂Cl 1-103 H F H NHSO₂CF₃ 1-104 H Cl H NHSO₂CF₃ 1-105 F F H NHSO₂CF₃ 1-106 F Cl H NHSO₂CF₃ 1-107 Cl F H NHSO₂CF₃ 1-108 Cl Cl H NHSO₂CF₃ 1-109 H F H N(SO₂CH₃)₂ 1-110 H Cl H N(SO₂CH₃)₂ 1-111 F F H N(SO₂CH₃)₂ 1-112 F Cl H N(SO₂CH₃)₂ 1-113 Cl F H N(SO₂CH₃)₂ 1-114 Cl Cl H N(SO₂CH₃)₂ 1-115 H F H N(CH₃)SO₂CH₃ 1-116 H Cl H N(CH₃)SO₂CH₃ 1-117 F F H N(CH₃)SO₂CH₃ 1-118 F Cl H N(CH₃)SO₂CH₃ 1-119 Cl F H N(CH₃)SO₂CH₃ 1-120 Cl Cl H N(CH₃)SO₂CH₃ 1-121 H F H N(CH₂C≡CH)SO₂CH₃ 1-122 H Cl H N(CH₂C≡CH)SO₂CH₃ 1-123 F F H N(CH₂C≡CH)SO₂CH₃ 1-124 F Cl H N(CH₂C≡CH)SO₂CH₃ 1-125 Cl F H N(CH₂C≡CH)SO₂CH₃

TABLE 6 X Y R¹ B 1-126 Cl Cl H N(CH₂C≡CH)SO₂CH₃ 1-127 H F H NHCOOCH₃ 1-128 H Cl H NHCOOCH₃ 1-129 F F H NHCOOCH₃ 1-130 F Cl H NHCOOCH₃ 1-131 Cl F H NHCOOCH₃ 1-132 Cl Cl H NHCOOCH₃ 1-133 H F H NHCOOC₂H₅ 1-134 H Cl H NHCOOC₂H₅ 1-135 F F H NHCOOC₂H₅ 1-136 F Cl H NHCOOC₂H₅ 1-137 Cl F H NHCOOC₂H₅ 1-138 Cl Cl H NHCOOC₂H₅ 1-139 H F H NHCOOnC₃H₇ 1-140 H Cl H NHCOOnC₃H₇ 1-141 F F H NHCOOnC₃H₇ 1-142 F Cl H NHCOOnC₃H₇ 1-143 Cl F H NHCOOnC₃H₇ 1-144 Cl Cl H NHCOOnC₃H₇ 1-145 H F H NHCOOiC₃H₇ 1-146 H Cl H NHCOOiC₃H₇ 1-147 F F H NHCOOiC₃H₇ 1-148 F Cl H NHCOOiC₃H₇ 1-149 Cl F H NHCOOiC₃H₇ 1-150 Cl Cl H NHCOOiC₃H₇

TABLE 7 X Y R¹ B 1-151 H F H NHCOOnC₄H₉ 1-152 H Cl H NHCOOnC₄H₉ 1-153 F F H NHCOOnC₄H₉ 1-154 F Cl H NHCOOnC₄H₉ 1-155 Cl F H NHCOOnC₄H₉ 1-156 Cl Cl H NHCOOnC₄H₉ 1-157 H F H NHCOOnC₅H₁₁ 1-158 H Cl H NHCOOnC₅H₁₁ 1-159 F F H NHCOOnC₅H₁₁ 1-160 F Cl H NHCOOnC₅H₁₁ 1-161 Cl F H NHCOOnC₅H₁₁ 1-162 Cl Cl H NHCOOnC₅H₁₁ 1-163 H F H NHCH₂COOCH₃ 1-164 H Cl H NHCH₂COOCH₃ 1-165 F F H NHCH₂COOCH₃ 1-166 F Cl H NHCH₂COOCH₃ 1-167 Cl F H NHCH₂COOCH₃ 1-168 Cl Cl H NHCH₂COOCH₃ 1-169 H F H NHCH₂COOC₂H₅ 1-170 H Cl H NHCH₂COOC₂H₅ 1-171 F F H NHCH₂COOC₂H₅ 1-172 F Cl H NHCH₂COOC₂H₅ 1-173 C1 F H NHCH₂COOC₂H₅ 1-174 Cl Cl H NHCH₂COOC₂H₅ 1-175 H F H NHCH₂COOnC₃H₇

TABLE 8 X Y R¹ B 1-176 H Cl H NHCH₂COOnC₃H₇ 1-177 F F H NHCH₂COOnC₃H₇ 1-178 F Cl H NHCH₂COOnC₃H₇ 1-179 Cl F H NHCH₂COOnC₃H₇ 1-180 Cl Cl H NHCH₂COOnC₃H₇ 1-181 H F H NHCH₂COOnC₄H₉ 1-182 H Cl H NHCH₂COOnC₄H₉ 1-183 F F H NHCH₂COOnC₄H₉ 1-184 F Cl H NHCH₂COOnC₄H₉ 1-185 Cl F H NHCH₂COOnC₄H₉ 1-186 Cl Cl H NHCH₂COOnC₄H₉ 1-187 H F H NHCH₂COOnC₅H₁₁ 1-188 H Cl H NHCH₂COOnC₅H₁₁ 1-189 F F H NHCH₂COOnC₅H₁₁ 1-190 F Cl H NHCH₂COOnC₅H₁₁ 1-191 Cl F H NHCH₂COOnC₅H₁₁ 1-192 Cl Cl H NHCH₂COOnC₅H₁₁ 1-193 H F H NHCH₂COOiC₃H₇ 1-194 H Cl H NHCH₂COOiC₃H₇ 1-195 F F H NHCH₂COOiC₃H₇ 1-196 F Cl H NHCH₂COOiC₃H₇ 1-197 Cl F H NHCH₂COOiC₃H₇ 1-198 Cl Cl H NHCH₂COOiC₃H₇ 1-199 H F H NHCH₂COOcC₅H₉ 1-200 H Cl H NHCH₂COOcC₅H₉

TABLE 9 X Y R¹ B 1-201 F F H NHCH₂COOcC₅H₉ 1-202 F Cl H NHCH₂COOcC₅H₉ 1-203 Cl F H NHCH₂COOcC₅H₉ 1-204 Cl Cl H NHCH₂COOcC₅H₉ 1-205 H F H NHCH₂COOcC₆H₁₁ 1-206 H Cl H NHCH₂COOcC₆H₁₁ 1-207 F F H NHCH₂COOcC₆H₁₁ 1-208 F Cl H NHCH₂COOcC₆H₁₁ 1-209 Cl F H NHCH₂COOcC₆H₁₁ 1-210 Cl Cl H NHCH₂COOcC₆H₁₁ 1-211 H F H NHCH(CH₃)COOCH₃ 1-212 H Cl H NHCH(CH₃)COOCH₃ 1-213 F F H NHCH(CH₃)COOCH₃ 1-214 F Cl H NHCH(CH₃)COOCH₃ 1-215 Cl F H NHCH(CH₃)COOCH₃ 1-216 Cl Cl H NHCH(CH₃)COOCH₃ 1-217 H F H NHCH(CH₃)COOC₂H₅ 1-218 H Cl H NHCH(CH₃)COOC₂H₅ 1-219 F F H NHCH(CH₃)COOC₂H₅ 1-220 F Cl H NHCH(CH₃)COOC₂H₅ 1-221 Cl F H NHCH(CH₃)COOC₂H₅ 1-222 Cl Cl H NHCH(CH₃)COOC₂H₅ 1-223 H F H NHCH(CH₃)COOnC₃H₇ 1-224 H Cl H NHCH(CH₃)COOnC₃H₇ 1-225 F F H NHCH(CH₃)COOnC₃H₇

TABLE 10 X Y R¹ B 1-226 F Cl H NHCH(CH₃)COOnC₃H₇ 1-227 Cl F H NHCH(CH₃)COOnC₃H₇ 1-228 Cl Cl H NHCH(CH₃)COOnC₃H₇ 1-229 H F H NHCH(CH₃)COOnC₄H₉ 1-230 H Cl H NHCH(CH₃)COOnC₄H₉ 1-231 F F H NHCH(CH₃)COOnC₄H₉ 1-232 F Cl H NHCH(CH₃)COOnC₄H₉ 1-233 Cl F H NHCH(CH₃)COOnC₄H₉ 1-234 Cl Cl H NHCH(CH₃)COOnC₄H₉ 1-235 H F H NHCH(CH₃)COOnC₅H₁₁ 1-236 H Cl H NHCH(CH₃)COOnC₅H₁₁ 1-237 F F H NHCH(CH₃)COOnC₅H₁₁ 1-238 F Cl H NHCH(CH₃)COOnC₅H₁₁ 1-239 Cl F H NHCH(CH₃)COOnC₅H₁₁ 1-240 Cl Cl H NHCH(CH₃)COOnC₅H₁₁ 1-241 H F H NHCH(CH₃)COOiC₃H₇ 1-242 H Cl H NHCH(CH₃)COOiC₃H₇ 1-243 F F H NHCH(CH₃)COOiC₃H₇ 1-244 F Cl H NHCH(CH₃)COOiC₃H₇ 1-245 Cl F H NHCH(CH₃)COOiC₃H₇ 1-246 Cl Cl H NHCH(CH₃)COOiC₃H₇ 1-247 H F H NHCH(CH₃)COOcC₅H₉ 1-248 H Cl H NHCH(CH₃)COOcC₅H₉ 1-249 F F H NHCH(CH₃)COOcC₅H₉ 1-250 F Cl H NHCH(CH₃)COOcC₅H₉

TABLE 11 X Y R¹ B 1-251 Cl F H NHCH(CH₃)COOcC₅H₉ 1-252 Cl Cl H NHCH(CH₃)COOcC₅H₉ 1-253 H F H NHCH(CH₃)COOcC₆H₁₁ 1-254 H Cl H NHCH(CH₃)COOcC₆H₁₁ 1-255 F F H NHCH(CH₃)COOcC₆H₁₁ 1-256 F Cl H NHCH(CH₃)COOcC₆H₁₁ 1-257 Cl F H NHCH(CH₃)COOcC₆H₁₁ 1-258 Cl Cl H NHCH(CH₃)COOcC₆H₁₁ 1-259 H F H OCH₃ 1-260 H Cl H OCH₃ 1-261 F F H OCH₃ 1-262 F Cl H OCH₃ 1-263 Cl F H OCH₃ 1-264 Cl Cl H OCH₃ 1-265 H F H OC₂H₅ 1-266 H Cl H OC₂H₅ 1-267 F F H OC₂H₅ 1-268 F Cl H OC₂H₅ 1-269 Cl F H OC₂H₅ 1-270 Cl Cl H OC₂H₅ 1-271 H F H OiC₃H₇ 1-272 H Cl H OiC₃H₇ 1-273 F F H OiC₃H₇ 1-274 F Cl H OiC₃H₇ 1-275 Cl F H OiC₃H₇

TABLE 12 X Y R¹ B 1-276 Cl Cl H OiC₃H₇ 1-277 H F H OnC₃H₇ 1-278 H Cl H OnC₃H₇ 1-279 F F H OnC₃H₇ 1-280 F Cl H OnC₃H₇ 1-281 Cl F H OnC₃H₇ 1-282 Cl Cl H OnC₃H₇ 1-283 H F H OCH₂CH₂Cl 1-284 H Cl H OCH₂CH₂Cl 1-285 F F H OCH₂CH₂Cl 1-286 F Cl H OCH₂CH₂Cl 1-287 Cl F H OCH₂CH₂Cl 1-288 Cl Cl H OCH₂CH₂Cl 1-289 H F H OCF₂CF₂H 1-290 H Cl H OCF₂CF₂H 1-291 F F H OCF₂CF₂H 1-292 F Cl H OCF₂CF₂H 1-293 Cl F H OCF₂CF₂H 1-294 Cl Cl H OCF₂CF₂H 1-295 H F H OcC₅H₉ 1-296 H Cl H OcC₅H₉ 1-297 F F H OcC₅H₉ 1-298 F Cl H OcC₅H₉ 1-299 Cl F H OcC₅H₉ 1-300 Cl Cl H OcC₅H₉

TABLE 13 X Y R¹ B 1-301 H F H OcC₆H₁₁ 1-302 H Cl H OcC₆H₁₁ 1-303 F F H OcC₆H₁₁ 1-304 F Cl H OcC₆H₁₁ 1-305 Cl F H OcC₆H₁₁ 1-306 Cl Cl H OcC₆H₁₁ 1-307 H F H OCH₂CH═CH₂ 1-308 H Cl H OCH₂CH═CH₂ 1-309 F F H OCH₂CH═CH₂ 1-310 F Cl H OCH₂CH═CH₂ 1-311 Cl F H OCH₂CH═CH₂ 1-312 Cl Cl H OCH₂CH═CH₂ 1-313 H F H OCH_(2CCl═CH) ₂ 1-314 H Cl H OCH₂CCl═CH₂ 1-315 F F H OCH₂CCl═CH₂ 1-316 F Cl H OCH₂CCl═CH₂ 1-317 Cl F H OCH₂CCl═CH₂ 1-318 Cl Cl H OCH₂CCl═CH₂ 1-319 H F H OCH₂CCl═CHCl 1-320 H Cl H OCH₂CCl═CHCl 1-321 F F H OCH₂CCl═CHCl 1-322 F Cl H OCH₂CCl═CHCl 1-323 Cl F H OCH₂CCl═CHCl 1-324 Cl Cl H OCH₂CCl═CHCl 1-325 H F H OCH(CH₃)CH═CH₂

TABLE 14 X Y R¹ B 1-326 H Cl H OCH(CH₃)CH═CH₂ 1-327 F F H OCH(CH₃)CH═CH₂ 1-328 F Cl H OCH(CH₃)CH═CH₂ 1-329 Cl F H OCH(CH₃)CH═CH₂ 1-330 Cl Cl H OCH(CH₃)CH═CH₂ 1-331 H F H OCH₂C(CH₃)═CH₂ 1-332 H Cl H OCH₂C(CH₃)═CH₂ 1-333 F F H OCH₂C(CH₃)═CH₂ 1-334 F Cl H OCH₂C(CH₃)═CH₂ 1-335 Cl F H OCH₂C(CH₃)═CH₂ 1-336 Cl Cl H OCH₂C(CH₃)═CH₂ 1-337 H F H OCH₂C≡CH 1-338 H Cl H OCH₂C≡CH 1-339 F F H OCH₂C≡CH 1-340 F Cl H OCH₂C≡CH 1-341 Cl F H OCH₂C≡CH 1-342 Cl Cl H OCH₂C≡CH 1-343 H F H OCH(CH₃)C≡CH 1-344 H Cl H OCH(CH₃)C≡CH 1-345 F F H OCH(CH₃)C≡CH 1-346 F Cl H OCH(CH₃)C≡CH 1-347 Cl F H OCH(CH₃)C≡CH 1-348 Cl Cl H OCH(CH₃)C≡CH 1-349 H F H OCH₂C≡CBr 1-350 H Cl H OCH₂C≡CBr

TABLE 15 X Y R¹ B 1-351 F F H OCH₂C≡CBr 1-352 F Cl H OCH₂C≡CBr 1-353 Cl F H OCH₂C≡CBr 1-354 Cl Cl H OCH₂C≡CBr 1-355 H F H OCH₂C≡CCl 1-356 H Cl H OCH₂C≡CCl 1-357 F F H OCH₂C≡CCl 1-358 F Cl H OCH₂C≡CCl 1-359 Cl F H OCH₂C≡CCl 1-360 Cl Cl H OCH₂C≡CCl 1-361 H F H OCH₂C≡CCH₂Cl 1-362 H Cl H OCH₂C≡CCH₂Cl 1-363 F F H OCH₂C≡CCH₂Cl 1-364 F Cl H OCH₂C≡CCH₂Cl 1-365 Cl F H OCH₂C≡CCH₂Cl 1-366 Cl Cl H OCH₂C≡CCH₂Cl 1-367 H F H OCH₂CN 1-368 H Cl H OCH₂CN 1-369 F F H OCH₂CN 1-370 F Cl H OCH₂CN 1-371 Cl F H OCH₂CN 1-372 Cl Cl H OCH₂CN 1-373 H F H OCH₂OCH₃ 1-374 H Cl H OCH₂OCH₃ 1-375 F F H OCH₂OCH₃

TABLE 16 X Y R¹ B 1-376 F Cl H OCH₂OCH₃ 1-377 Cl F H OCH₂OCH₃ 1-378 Cl Cl H OCH₂OCH₃ 1-379 H F H OCH₂OC₂H₅ 1-380 H Cl H OCH₂OC₂H₅ 1-381 F F H OCH₂OC₂H₅ 1-382 F Cl H OCH₂OC₂H₅ 1-383 Cl F H OCH₂OC₂H₅ 1-384 Cl Cl H OCH₂OC₂H₅ 1-385 H F H OCH₂SCH₃ 1-386 H Cl H OCH₂SCH₃ 1-387 F F H OCH₂SCH₃ 1-388 F Cl H OCH₂SCH₃ 1-389 Cl F H OCH₂SCH₃ 1-390 Cl Cl H OCH₂SCH₃ 1-391 H F H OCH₂COOH 1-392 H Cl H OCH₂COOH 1-393 F F H OCH₂COOH 1-394 F Cl H OCH₂COOH 1-395 Cl F H OCH₂COOH 1-396 Cl Cl H OCH₂COOH 1-397 H F H OCH₂COOCH₃ 1-398 H Cl H OCH₂COOCH₃ 1-399 F F H OCH₂COOCH₃ 1-400 F Cl H OCH₂COOCH₃

TABLE 17 X Y R¹ B 1-401 Cl F H OCH₂COOCH₃ 1-402 Cl Cl H OCH₂COOCH₃ 1-403 H F H OCH₂COOC₂H₅ 1-404 H Cl H OCH₂COOC₂H₅ 1-405 F F H OCH₂COOC₂H₅ 1-406 F Cl H OCH₂COOC₂H₅ 1-407 Cl F H OCH₂COOC₂H₅ 1-408 Cl Cl H OCH₂COOC₂H₅ 1-409 H F H OCH₂COO_(n)C₃H₇ 1-410 H Cl H OCH₂COO_(n)C₃H₇ 1-411 F F H OCH₂COO_(n)C₃H₇ 1-412 F Cl H OCH₂COO_(n)C₃H₇ 1-413 Cl F H OCH₂COO_(n)C₃H₇ 1-414 Cl Cl H OCH₂COO_(n)C₃H₇ 1-415 H F H OCH₂COO_(n)C₄H₉ 1-416 H Cl H OCH₂COO_(n)C₄H₉ 1-417 F F H OCH₂COO_(n)C₄H₉ 1-418 F Cl H OCH₂COO_(n)C₄H₉ 1-419 Cl F H OCH₂COO_(n)C₄H₉ 1-420 Cl Cl H OCH₂COO_(n)C₄H₉ 1-421 H F H OCH₂COO_(n)C₅H₁₁ 1-422 H Cl H OCH₂COO_(n)C₅H₁₁ 1-423 F F H OCH₂COO_(n)C₅H₁₁ 1-424 F Cl H OCH₂COO_(n)C₅H₁₁ 1-425 Cl F H OCH₂COO_(n)C₅H₁₁

TABLE 18 X Y R¹ B 1-426 Cl Cl H OCH₂COO_(n)C₅H11 1-427 H F H OCH₂COO_(i)C₃H₇ 1-428 H Cl H OCH₂COO_(i)C₃H₇ 1-429 F F H OCH₂COO_(i)C₃H₇ 1-430 F Cl H OCH₂COO_(i)C₃H₇ 1-431 Cl F H OCH₂COO_(i)C₃H₇ 1-432 Cl Cl H OCH₂COO_(i)C₃H₇ 1-433 H F H OCH₂COO_(c)C₅H₉ 1-434 H Cl H OCH₂COO_(c)C₅H₉ 1-435 F F H OCH₂COO_(c)C₅H₉ 1-436 F Cl H OCH₂COO_(c)C₅H₉ 1-437 Cl F H OCH₂COO_(c)C₅H₉ 1-438 Cl Cl H OCH₂COO_(c)C₅H₉ 1-439 H F H OCH₂COO_(c)C₆H₁₁ 1-440 H Cl H OCH₂COO_(c)C₆H₁₁ 1-441 F F H OCH₂COO_(c)C₆H₁₁ 1-442 F Cl H OCH₂COO_(c)C₆H₁₁ 1-443 Cl F H OCH₂COO_(c)C₆H₁₁ 1-444 Cl Cl H OCH₂COO_(c)C₆H₁₁ 1-445 H F H OCH(CH₃)COOH 1-446 H Cl H OCH(CH₃)COOH 1-447 F F H OCH(CH₃)COOH 1-448 F Cl H OCH(CH₃)COOH 1-449 Cl F H OCH(CH₃)COOH 1-450 Cl Cl H OCH(CH₃)COOH

TABLE 19 X Y R¹ B 1-451 H F H OCH(CH₃)COOCH₃ 1-452 H Cl H OCH(CH₃)COOCH₃ 1-453 F F H OCH(CH₃)COOCH₃ 1-454 F Cl H OCH(CH₃)COOCH₃ 1-455 Cl F H OCH(CH₃)COOCH₃ 1-456 Cl Cl H OCH(CH₃)COOCH₃ 1-457 H F H OCH(CH₃)COOC₂H₅ 1-458 H Cl H OCH(CH₃)COOC₂H₅ 1-459 F F H OCH(CH₃)COOC₂H₅ 1-460 F Cl H OCH(CH₃)COOC₂H₅ 1-461 Cl F H OCH(CH₃)COOC₂H₅ 1-462 Cl Cl H OCH(CH₃)COOC₂H₅ 1-463 H F H OCH(CH₃)COO_(n)C₃H₇ 1-464 H Cl H OCH(CH₃)COO_(n)C₃H₇ 1-465 F F H OCH(CH₃)COO_(n)C₃H₇ 1-466 F Cl H OCH(CH₃)COO_(n)C₃H₇ 1-467 Cl F H OCH(CH₃)COO_(n)C₃H₇ 1-468 Cl Cl H OCH(CH₃)COO_(n)C₃H₇ 1-469 H F H OCH(CH₃)COO_(n)C₄H₉ 1-470 H Cl H OCH(CH₃)COO_(n)C₄H₉ 1-471 F F H OCH(CH₃)COO_(n)C₄H₉ 1-472 F Cl H OCH(CH₃)COO_(n)C₄H₉ 1-473 Cl F H OCH(CH₃)COO_(n)C₄H₉ 1-474 Cl Cl H OCH(CH₃)COO_(n)C₄H₉ 1-475 H F H OCH(CH₃)COO_(n)C₅H₁₁

TABLE 20 X Y R¹ B 1-476 H Cl 0 H OCH(CH₃)COO_(n)C₅H₁₁ 1-477 F F H OCH(CH₃)COO_(n)C₅H₁₁ 1-478 F Cl H OCH(CH₃)COO_(n)C₅H₁₁ 1-479 Cl F H OCH(CH₃)COO_(n)C₅H₁₁ 1-480 Cl Cl H OCH(CH₃)COO_(n)C₅H₁₁ 1-481 H F H OCH(CH₃)COO_(i)C₃H₇ 1-482 H Cl H OCH(CH₃)COO_(i)C₃H₇ 1-483 F F H OCH(CH₃)COO_(i)C₃H₇ 1-484 F Cl H OCH(CH₃)COO_(i)C₃H₇ 1-485 Cl F H OCH(CH₃)COO_(i)C₃H₇ 1-486 Cl Cl H OCH(CH₃)COO_(i)C₃H₇ 1-487 H F H OCH(CH₃)COO_(c)C₅H₉ 1-488 H Cl H OCH(CH₃)COO_(c)C₅H₉ 1-489 F F H OCH(CH₃)COO_(c)C₅H₉ 1-490 F Cl H OCH(CH₃)COO_(c)C₅H₉ 1-491 Cl F H OCH(CH₃)COO_(c)C₅H₉ 1-492 Cl Cl H OCH(CH₃)COO_(c)C₅H₉ 1-493 H F H OCH(CH₃)COO_(c)C₆H₁₁ 1-494 H Cl H OCH(CH₃)COO_(c)C₆H₁₁ 1-495 F F H OCH(CH₃)COO_(c)C₆H₁₁ 1-496 F Cl H OCH(CH₃)COO_(c)C₆H₁₁ 1-497 Cl F H OCH(CH₃)COO_(c)C₆H₁₁ 1-498 Cl Cl H OCH(CH₃)COO_(c)C₆H₁₁ 1-499 H F H OCH₂CONH₂ 1-500 H Cl H OCH₂CONH₂

TABLE 21 X Y R¹ B 1-501 F F H OCH₂CONH₂ 1-502 F Cl H OCH₂CONH₂ 1-503 Cl F H OCH₂CONH₂ 1-504 Cl Cl H OCH₂CONH₂ 1-505 H F H OCH₂CONHCH₃ 1-506 H Cl H OCH₂CONHCH₃ 1-507 F F H OCH₂CONHCH₃ 1-508 F Cl H OCH₂CONHCH₃ 1-509 Cl F H OCH₂CONHCH₃ 1-510 Cl Cl H OCH₂CONHCH₃ 1-511 H F H OCH₂CON(CH₃)₂ 1-512 H Cl H OCH₂CON(CH₃)₂ 1-513 F F H OCH₂CON(CH₃)₂ 1-514 F Cl H OCH₂CON(CH₃)₂ 1-515 Cl F H OCH₂CON(CH₃)₂ 1-516 Cl Cl H OCH₂CON(CH₃)₂ 1-517 H F H OCH₂CON(C₂H₅)₂ 1-518 H Cl H OCH₂CON(C₂H₅)₂ 1-519 F F H OCH₂CON(C₂H₅)₂ 1-520 F Cl H OCH₂CON(C₂H₅)₂ 1-521 Cl F H OCH₂CON(C₂H₅)₂ 1-522 Cl Cl H OCH₂CON(C₂H₅)₂ 1-523 H F H OCH₂CON(CH₃)C₂H₅ 1-524 H Cl H OCH₂CON(CH₃)C₂H₅ 1-525 F F H OCH₂CON(CH₃)C₂H₅

TABLE 22 X Y R¹ B 1-526 F Cl H OCH₂CON(CH₃)C₂H₅ 1-527 Cl F H OCH₂CON(CH₃)C₂H₅ 1-528 Cl Cl H OCH₂CON(CH₃)C₂H₅ 1-529 H F H OCH₂CON(tetramethylene) 1-530 H Cl H OCH₂CON(tetramethylene) 1-531 F F H OCH₂CON(tetramethylene) 1-532 F Cl H OCH₂CON(tetramethylene) 1-533 Cl F H OCH₂CON(tetramethylene) 1-534 CI Cl H OCH₂CON(tetramethylene) 1-535 H F H OCH₂CON(pentamethylene) 1-536 H Cl H OCH₂CON(pentamethylene) 1-537 F F H OCH₂CON(pentamethylene) 1-538 F Cl H OCH₂CON(pentamethylene) 1-539 Cl F H OCH₂CON(pentamethylene) 1-540 Cl Cl H OCH₂CON(pentamethylene) 1-541 H F H OCH₂CON(ethyleneoxyethylene) 1-542 H Cl H OCH₂CON(ethyleneoxyethylene) 1-543 F F H OCH₂CON(ethyleneoxyethylene) 1-544 F Cl H OCH₂CON(ethyleneoxyethylene) 1-545 Cl F H OCH₂CON(ethyleneoxyethylene) 1-546 Cl Cl H OCH₂CON(ethyleneoxyethylene) 1-547 H F H OCH(CH₃)CONH₂ 1-548 H Cl H OCH(CH₃)CONH₂ 1-549 F F H OCH(CH₃)CONH₂ 1-550 F Cl H OCH(CH₃)CONH₂

TABLE 23 X Y R¹ B 1-551 Cl F H OCH(CH₃)CONH₂ 1-552 Cl Cl H OCH(CH₃)CONH₂ 1-553 H F H OCH(CH₃)CONHCH₃ 1-554 H Cl H OCH(CH₃)CONHCH₃ 1-555 F F H OCH(CH₃)CONHCH₃ 1-556 F Cl H OCH(CH₃)CONHCH₃ 1-557 Cl F H OCH(CH₃)CONHCH₃ 1-558 Cl Cl H OCH(CH₃)CONHCH₃ 1-559 H F H OCH(CH₃)CON(CH₃)₂ 1-560 H Cl H OCH(CH₃)CON(CH₃)₂ 1-561 F F H OCH(CH₃)CON(CH₃)₂ 1-562 F Cl H OCH(CH₃)CON(CH₃)₂ 1-563 Cl F H OCH(CH₃)CON(CH₃)₂ 1-564 Cl Cl H OCH(CH₃)CON(CH₃)₂ 1-565 H F H OCH(CH₃)CON(C₂H₅)₂ 1-566 H Cl H OCH(CH₃)CON(C₂H₅)₂ 1-567 F F H OCH(CH₃)CON(C₂H₅)₂ 1-568 F Cl H OCH(CH₃)CON(C₂H₅)₂ 1-569 Cl F H OCH(CH₃)CON(C₂H₅)₂ 1-570 Cl Cl H OCH(CH₃)CON(C₂H₅)₂ 1-571 H F H OCH(CH₃)CON(CH₃)C₂H₅ 1-572 H Cl H OCH(CH₃)CON(CH₃)C₂H₅ 1-573 F F H OCH(CH₃)CON(CH₃)C₂H₅ 1-574 F Cl H OCH(CH₃)CON(CH₃)C₂H₅ 1-575 Cl F H OCH(CH₃)CON(CH₃)C₂H₅

TABLE 24 X Y R¹ B 1-576 Cl Cl H OCH(CH₃)CON(CH₃)C₂H₅ 1-577 H F H OCH(CH₃)CON(tetramethylene) 1-578 H Cl H OCH(CH₃)CON(tetramethylene) 1-579 F F H OCH(CH₃)CON(tetramethylene) 1-580 F Cl H OCH(CH₃)CON(tetramethylene) 1-581 Cl F H OCH(CH₃)CON(tetramethylene) 1-582 Cl Cl H OCH(CH₃)CON(tetramethylene) 1-583 H F H OCH(CH₃)CON(pentamethylene) 1-584 H Cl H OCH(CH₃)CON(pentamethylene) 1-585 F F H OCH(CH₃)CON(pentamethylene) 1-586 F Cl H OCH(CH₃)CON(pentamethylene) 1-587 Cl F H OCH(CH₃)CON(pentamethylene) 1-588 Cl Cl H OCH(CH₃)CON(pentamethylene) 1-589 H F H OCH(CH₃)CON(ethyleneoxyethylene) 1-590 H Cl H OCH(CH₃)CON(ethyleneoxyethylene) 1-591 F F H OCH(CH₃)CON(ethyleneoxyethylene) 1-592 F Cl H OCH(CH₃)CON(ethyleneoxyethylene) 1-593 Cl F H OCH(CH₃)CON(ethyleneoxyethylene) 1-594 Cl Cl H OCH(CH₃)CON(ethyleneoxyethylene) 1-595 H F H OCH₂COON(CH₃)₂ 1-596 H Cl H OCH₂COON(CH₃)₂ 1-597 F F H OCH₂COON(CH₃)₂ 1-598 F Cl H OCH₂COON(CH₃)₂ 1-599 Cl F H OCH₂COON(CH₃)₂ 1-600 Cl Cl H OCH₂COON(CH₃)₂

TABLE 25 X Y R¹ B 1-601 H F H OCH₂COON(C₂H₅)₂ 1-602 H Cl H OCH₂COON(C₂H₅)₂ 1-603 F F H OCH₂COON(C₂H₅)₂ 1-604 F Cl H OCH₂COON(C₂H₅)₂ 1-605 Cl F H OCH₂COON(C₂H₅)₂ 1-606 Cl Cl H OCH₂COON(C₂H₅)₂ 1-607 H F H OCH(CH₃)COON(CH₃)₂ 1-608 H Cl H OCH(CH₃)COON(CH₃)₂ 1-609 F F H OCH(CH₃)COON(CH₃)₂ 1-610 F Cl H OCH(CH₃)COON(CH₃)₂ 1-611 Cl F H OCH(CH₃)COON(CH₃)₂ 1-612 Cl Cl H OCH(CH₃)COON(CH₃)₂ 1-613 H F H OCH(CH₃)COON(C₂H₅)₂ 1-614 H Cl H OCH(CH₃)COON(C₂H₅)₂ 1-615 F F H OCH(CH₃)COON(C₂H₅)₂ 1-616 F Cl H OCH(CH₃)COON(C₂H₅)₂ 1-617 Cl F H OCH(CH₃)COON(C₂H₅)₂ 1-618 Cl Cl H OCH(CH₃)COON(C₂H₅)₂ 1-619 H F H SCH₃ 1-620 H Cl H SCH₃ 1-621 F F H SCH₃ 1-622 F Cl H SCH₃ 1-623 Cl F H SCH₃ 1-624 Cl Cl H SCH₃ 1-625 H F H SC₂H₅

TABLE 26 X Y R¹ B 1-626 H Cl H SC₂H₅ 1-627 F F H SC₂H₅ 1-628 F Cl H SC₂H₅ 1-629 Cl F H SC₂H₅ 1-630 Cl Cl H SC₂H₅ 1-631 H F H SiC₃H₇ 1-632 H Cl H SiC₃H₇ 1-633 F F H SiC₃H₇ 1-634 F Cl H SiC₃H₇ 1-635 Cl F H SiC₃H₇ 1-636 Cl Cl H SiC₃H₇ 1-637 H F H SnC₃H₇ 1-638 H Cl H SnC₃H₇ 1-639 F F H SnC₃H₇ 1-640 F Cl H SnC₃H₇ 1-641 Cl F H SnC₃H₇ 1-642 Cl Cl H SnC₃H₇ 1-643 H F H SCH₂CH₂Cl 1-644 H Cl H SCH₂CH₂Cl 1-645 F F H SCH₂CH₂Cl 1-646 F Cl H SCH₂CH₂Cl 1-647 Cl F H SCH₂CH₂Cl 1-648 Cl Cl H SCH₂CH₂Cl 1-649 H F H ScC₅H₉ 1-650 H Cl H ScC₅H₉

TABLE 27 X Y R¹ B 1-651 F F H ScC₅H₉ 1-652 F Cl H ScC₅H₉ 1-653 Cl F H ScC₅H₉ 1-654 Cl Cl H ScC₅H₉ 1-655 H F H ScC₆H₁₁ 1-656 H Cl H ScC₆H₁₁ 1-657 F F H ScC₆H₁₁ 1-658 F Cl H ScC₆H₁₁ 1-659 Cl F H ScC₆H₁₁ 1-660 Cl Cl H ScC₆H₁₁ 1-661 H F H SCH₂CH═CH₂ 1-662 H Cl H SCH₂CH═CH₂ 1-663 F F H SCH₂CH═CH₂ 1-664 F Cl H SCH₂CH═CH₂ 1-665 Cl F H SCH₂CH═CH₂ 1-666 Cl Cl H SCH₂CH═CH₂ 1-667 H F H SCH₂CCl═CH₂ 1-668 H Cl H SCH₂CCl═CH₂ 1-669 F F H SCH₂CCl═CH₂ 1-670 F Cl H SCH₂CCl═CH₂ 1-671 Cl F H SCH₂CCl═CH₂ 1-672 Cl Cl H SCH₂CCl═CH₂ 1-673 H F H SCH₂CCl═CHCl 1-674 H Cl H SCH₂CCl═CHCl 1-675 F F H SCH₂CCl═CHCl

TABLE 28 X Y R¹ B 1-676 F Cl H SCH₂CCl═CHCl 1-677 Cl F H SCH₂CCl═CHCl 1-678 Cl Cl H SCH₂CCl═CHCl 1-679 H F H SCH(CH₃)CH═CH₂ 1-680 H Cl H SCH(CH₃)CH═CH₂ 1-681 F F H SCH(CH₃)CH═CH₂ 1-682 F Cl H SCH(CH₃)CH═CH₂ 1-683 Cl F H SCH(CH₃)CH═CH₂ 1-684 Cl Cl H SCH(CH₃)CH═CH₂ 1-685 H F H SCH₂C≡CH 1-686 H Cl H SCH₂C≡CH 1-687 F F H SCH₂C≡CH 1-688 F Cl H SCH₂C≡CH 1-689 Cl F H SCH₂C≡CH 1-690 Cl Cl H SCH₂C≡CH 1-691 H F H SCH(CH₃)C≡CH 1-692 H Cl H SCH(CH₃)C≡CH 1-693 F F H SCH(CH₃)C≡CH 1-694 F Cl H SCH(CH₃)C≡CH 1-695 Cl F H SCH(CH₃)C≡CH 1-696 Cl Cl H SCH(CH₃)C≡CH 1-697 H F H SCH₂COOH 1-698 H Cl H SCH₂COOH 1-699 F F H SCH₂COOH 1-700 F Cl H SCH₂COOH

TABLE 29 X Y R¹ B 1-701 Cl F H SCH₂COOH 1-702 Cl Cl H SCH₂COOH 1-703 H F H SCH₂COOCH₃ 1-704 H Cl H SCH₂COOCH₃ 1-705 F F H SCH₂COOCH₃ 1-706 F Cl H SCH₂COOCH₃ 1-707 Cl F H SCH₂COOCH₃ 1-708 Cl Cl H SCH₂COOCH₃ 1-709 H F H SCH₂COOC₂H₅ 1-710 H Cl H SCH₂COOC₂H₅ 1-711 F F H SCH₂COOC₂H₅ 1-712 F Cl H SCH₂COOC₂H₅ 1-713 Cl F H SCH₂COOC₂H₅ 1-714 Cl Cl H SCH₂COOC₂H₅ 1-715 H F H SCH₂COO_(n)C₃H₇ 1-716 H Cl H SCH₂COO_(n)C₃H₇ 1-717 F F H SCH₂COO_(n)C₃H₇ 1-718 F Cl H SCH₂COO_(n)C₃H₇ 1-719 Cl F H SCH₂COO_(n)C₃H₇ 1-720 Cl Cl H SCH₂COO_(n)C₃H₇ 1-721 H F H SCH₂COO_(n)C₄H₉ 1-722 H Cl W SCH₂COO_(n)C₄H₉ 1-723 F F H SCH₂COO_(n)C₄H₉ 1-724 F Cl H SCH₂COO_(n)C₄H₉ 1-725 Cl F H SCH₂COO_(n)C₄H₉

TABLE 30 X Y R¹ B 1-726 Cl Cl H SCH₂COO_(n)C₄H₉ 1-727 H F H SCH₂COO_(n)C₅H₁₁ 1-728 H Cl H SCH₂COO_(n)C₅H₁₁ 1-729 F F H SCH₂COO_(n)C₅H₁₁ 1-730 F Cl H SCH₂COO_(n)C₅H₁₁ 1-731 Cl F H SCH₂COO_(n)C₅H₁₁ 1-732 Cl Cl H SCH₂COO_(n)C₅H₁₁ 1-733 H F H SCH₂COO_(i)C₃H₇ 1-734 H Cl H SCH₂COO_(i)C₃H₇ 1-735 F F H SCH₂COO_(i)C₃H₇ 1-736 F Cl H SCH₂COO_(i)C₃H₇ 1-737 Cl F H SCH₂COO_(i)C₃H₇ 1-738 Cl Cl H SCH₂COO_(i)C₃H₇ 1-739 H F H SCH₂COO_(c)C₅H₉ 1-740 H Cl H SCH₂COO_(c)C₅H₉ 1-741 F F H SCH₂COO_(c)C₅H₉ 1-742 F Cl H SCH₂COO_(c)C₅H₉ 1-743 Cl F H SCH₂COO_(c)C₅H₉ 1-744 Cl Cl H SCH₂COO_(c)C₅H₉ 1-745 H F H SCH₂COO_(c)C₆H₁₁ 1-746 H Cl H SCH₂COO_(c)C₆H₁₁ 1-747 F F H SCH₂COO_(c)C₆H₁₁ 1-748 F Cl H SCH₂COO_(c)C₆H₁₁ 1-749 Cl F H SCH₂COO_(c)C₆H₁₁ 1-750 Cl Cl H SCH₂COO_(c)C₆H₁₁

TABLE 31 X Y R¹ B 1-751 H F H SCH(CH₃)COOH 1-752 H Cl H SCH(CH₃)COOH 1-753 F F H SCH(CH₃)COOH 1-754 F Cl H SCH(CH₃)COOH 1-755 Cl F H SCH(CH₃)COOH 1-756 Cl Cl H SCH(CH₃)COOH 1-757 H F H SCH(CH₃)COOCH₃ 1-758 H Cl H SCH(CH₃)COOCH₃ 1-759 F F H SCH(CH₃)COOCH₃ 1-760 F Cl H SCH(CH₃)COOCH₃ 1-761 Cl F H SCH(CH₃)COOCH₃ 1-762 Cl Cl H SCH(CH₃)COOCH₃ 1-763 H F H SCH(CH₃)COOC₂H₅ 1-764 H Cl H SCH(CH₃)COOC₂H₅ 1-765 F F H SCH(CH₃)COOC₂H₅ 1-766 F Cl H SCH(CH₃)COOC₂H₅ 1-767 Cl F H SCH(CH₃)COOC₂H₅ 1-768 Cl Cl H SCH(CH₃)COOC₂H₅ 1-769 H F H SCH(CH₃)COO_(n)C₃H₇ 1-770 H Cl H SCH(CH₃)COO_(n)C₃H₇ 1-771 F F H SCH(CH₃)COO_(n)C₃H₇ 1-772 F Cl H SCH(CH₃)COO_(n)C₃H₇ 1-773 Cl F H SCH(CH₃)COO_(n)C₃H₇ 1-774 Cl Cl H SCH(CH₃)COO_(n)C₃H₇ 1-775 H F H SCH(CH₃)COO_(n)C₄H₉

TABLE 32 X Y R¹ B 1-776 H Cl H SCH(CH₃)COO_(n)C₄H₉ 1-777 F F H SCH(CH₃)COO_(n)C₄H₉ 1-778 F Cl H SCH(CH₃)COO_(n)C₄H₉ 1-779 Cl F H SCH(CH₃)COO_(n)C₄H₉ 1-780 Cl Cl H SCH(CH₃)COO_(n)C₄H₉ 1-781 H F H SCH(CH₃)COO_(n)C₅H₁₁ 1-782 H Cl H SCH(CH₃)COO_(n)C₅H₁₁ 1-783 F F H SCH(CH₃)COO_(n)C₅H₁₁ 1-784 F Cl H SCH(CH₃)COO_(n)C₅H₁₁ 1-785 Cl F H SCH(CH₃)COO_(n)C₅H₁₁ 1-786 Cl Cl H SCH(CH₃)COO_(n)C₅H₁₁ 1-787 H F H SCH(CH₃)COO_(i)C₃H₇ 1-788 H Cl H SCH(CH₃)COO_(i)C₃H₇ 1-789 F F H SCH(CH₃)COO_(i)C₃H₇ 1-790 F Cl H SCH(CH₃)COO_(i)C₃H₇ 1-791 Cl F H SCH(CH₃)COO_(i)C₃H₇ 1-792 Cl Cl H SCH(CH₃)COO_(i)C₃H₇ 1-793 H F H SCH(CH₃)COO_(c)C₅H₉ 1-794 H Cl H SCH(CH₃)COO_(c)C₅H₉ 1-795 F F H SCH(CH₃)COO_(c)C₅H₉ 1-796 F Cl H SCH(CH₃)COO_(c)C₅H₉ 1-797 Cl F H SCH(CH₃)COO_(c)C₅H₉ 1-798 Cl Cl H SCH(CH₃)COO_(c)C₅H₉ 1-799 H F H SCH(CH₃)COO_(c)C₆H₁₁ 1-800 H Cl H SCH(CH₃)COO_(c)C₆H₁₁

TABLE 33 X Y R¹ B 1-801 F F H SCH(CH₃)COO_(c)C₆H₁₁ 1-802 F Cl H SCH(CH₃)COO_(c)C₆H₁₁ 1-803 Cl F H SCH(CH₃)COO_(c)C₆H₁₁ 1-804 Cl Cl H SCH(CH₃)COO_(c)C₆H₁₁ 1-805 H F H SCH₂CONH₂ 1-806 H Cl H SCH₂CONH₂ 1-807 F F H SCH₂CONH₂ 1-808 F Cl H SCH₂CONH₂ 1-809 Cl F H SCH₂CONH₂ 1-810 Cl Cl H SCH₂CONH₂ 1-811 H F H SCH₂CONHCH₃ 1-812 H Cl H SCH₂CONHCH₃ 1-813 F F H SCH₂CONHCH₃ 1-814 F Cl H SCH₂CONHCH₃ 1-815 Cl F H SCH₂CONHCH₃ 1-816 Cl Cl H SCH₂CONHCH₃ 1-817 H F H SCH₂CON(CH₃)₂ 1-818 H Cl H SCH₂CON(CH₃)₂ 1-819 F F H SCH₂CON(CH₃)₂ 1-820 F Cl H SCH₂CON(CH₃)₂ 1-821 Cl F H SCH₂CON(CH₃)₂ 1-822 Cl Cl H SCH₂CON(CH₃)₂ 1-823 H F H SCH₂CON(C₂H₅)₂ 1-824 H Cl H SCH₂CON(C₂H₅)₂ 1-825 F F H SCH₂CON(C₂H₅)₂

TABLE 34 X Y R¹ B 1-826 F Cl H SCH₂CON(C_(2H) ₅)₂ 1-827 Cl F H SCH₂CON(C₂H₅)₂ 1-828 Cl Cl H SCH₂CON(C₂H₅)₂ 1-829 H F H SCH₂CON(CH₃)C_(2H) ₅ 1-830 H Cl H SCH₂CON(CH₃)C_(2H) ₅ 1-831 F F H SCH₂CON(CH₃)C_(2H) ₅ 1-832 F Cl H SCH₂CON(CH₃)C_(2H) ₅ 1-833 Cl F H SCH₂CON(CH₃)C_(2H) ₅ 1-834 Cl Cl H SCH₂CON(CH₃)C_(2H) ₅ 1-835 H F H SCH₂CON(tetramethylene) 1-836 H Cl H SCH₂CON(tetramethylene) 1-837 F F H SCH₂CON(tetramethylene) 1-838 F Cl H SCH₂CON(tetramethylene) 1-839 Cl F H SCH₂CON(tetramethylene) 1-840 Cl Cl H SCH₂CON(tetramethylene) 1-841 H F H SCH₂CON(pentamethylene) 1-842 H Cl H SCH₂CON(pentamethylene) 1-843 F F H SCH₂CON(pentamethylene) 1-844 F Cl H SCH₂CON(pentamethylene) 1-845 Cl F H SCH₂CON(pentamethylene) 1-846 Cl Cl H SCH₂CON(pentamethylene) 1-847 H F H SCH₂CON(ethyleneoxyethylene) 1-848 H Cl H SCH₂CON(ethyleneoxyethylene) 1-849 F F H SCH₂CON(ethyleneoxyethylene) 1-850 F Cl H SCH₂CON(ethyleneoxyethylene)

TABLE 35 X Y R¹ B 1-851 Cl F H SCH₂CON(ethyleneoxyethylene) 1-852 Cl Cl H SCH₂CON(ethyleneoxyethylene) 1-853 H F H SCH(CH₃)CONH₂ 1-854 H Cl H SCH(CH₃)CONH₂ 1-855 F F H SCH(CH₃)CONH₂ 1-856 F Cl H SCH(CH₃)CONH₂ 1-857 Cl F H SCH(CH₃)CONH₂ 1-858 Cl Cl H SCH(CH₃)CONH₂ 1-859 H F H SCH(CH₃)CONHCH₃ 1-860 H Cl H SCH(CH₃)CONHCH₃ 1-861 F F H SCH(CH₃)CONHCH₃ 1-862 F Cl H SCH(CH₃)CONHCH₃ 1-863 Cl F H SCH(CH₃)CONHCH₃ 1-864 Cl Cl H SCH(CH₃)CONHCH₃ 1-865 H F H SCH(CH₃)CON(CH₃)₂ 1-866 H Cl H SCH(CH₃)CON(CH₃)₂ 1-867 F F H SCH(CH₃)CON(CH₃)₂ 1-868 F Cl H SCH(CH₃)CON(CH₃)₂ 1-869 Cl F H SCH(CH₃)CON(CH₃)₂ 1-87O Cl Cl H SCH(CH₃)CON(CH₃)₂ 1-871 H F H SCH(CH₃)CON(C₂H₅)₂ 1-872 H Cl H SCH(CH₃)CON(C₂H₅)₂ 1-873 F F H SCH(CH₃)CON(C₂H₅)₂ 1-874 F Cl H SCH(CH₃)CON(C₂H₅)₂ 1-875 Cl F H SCH(CH₃)CON(C₂H₅)₂

TABLE 36 X Y R¹ B 1-876 Cl Cl H SCH(CH₃)CON(C₂H₅)₂ 1-877 H F H SCH(CH₃)CON(CH₃)C₂H₅ 1-878 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 1-879 F F H SCH(CH₃)CON(CH₃)C₂H₅ 1-880 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 1-881 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 1-882 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 1-883 H F H SCH(CH₃)CON(CH₃)C₂H₅ 1-884 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 1-885 F F H SCH(CH₃)CON(CH₃)C₂H₅ 1-886 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 1-887 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 1-888 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 1-889 H F H SCH(CH₃)CON(tetramethylene) 1-890 H Cl H SCH(CH₃)CON(tetramethylene) 1-891 F F H SCH(CH₃)CON(tetramethylene) 1-892 F Cl H SCH(CH₃)CON(tetramethylene) 1-893 Cl F H SCH(CH₃)CON(tetramethylene) 1-894 Cl Cl H SCH(CH₃)CON(tetramethylene) 1-895 H F H SCH(CH₃)CON(pentamethylene) 1-896 H Cl H SCH(CH₃)CON(pentamethylene) 1-897 F F H SCH(CH₃)CON(pentamethylene) 1-898 F Cl H SCH(CH₃)CON(pentamethylene) 1-899 Cl F H SCH(CH₃)CON(pentamethylene) 1-900 Cl Cl H SCH(CH₃)CON(pentamethylene)

TABLE 37 X Y R¹ B 1-901 H F H SCH(CH₃)CON(ethyleneoxyethylene) 1-902 H Cl H SCH(CH₃)CON(ethyleneoxyethylene) 1-903 F F H SCH(CH₃)CON(ethyleneoxyethylene) 1-904 F Cl H SCH(CH₃)CON(ethyleneoxyethylene) 1-905 Cl F H SCH(CH₃)CON(ethyleneoxyethylene) 1-906 Cl Cl H SCH(CH₃)CON(ethyleneoxyethylene) 1-907 H F H SO₂OCH₃ 1-908 H Cl H SO₂OCH₃ 1-909 F F H SO₂OCH₃ 1-910 F Cl H SO₂OCH₃ 1-911 Cl F H SO₂OCH₃ 1-912 Cl Cl H SO₂OCH₃ 1-913 H F H SO₂OC₂H₅ 1-914 H Cl H SO₂OC₂H₅ 1-915 F F H SO₂OC₂H₅ 1-916 F Cl H SO₂OC₂H₅ 1-917 Cl F H SO₂OC₂H₅ 1-918 Cl Cl H SO₂OC₂H₅ 1-919 H F H SO₂OiC₃H₇ 1-920 H Cl H SO₂OiC₃H₇ 1-921 F F H SO₂OiC₃H₇ 1-922 F Cl H SO₂OiC₃H₇ 1-923 Cl F H SO₂OiC₃H₇ 1-924 Cl Cl H SO₂OiC₃H₇ 1-925 H F H SO₂OCH₂CH═CH₂

TABLE 38 X Y R¹ B 1-926 H Cl H SO₂OCH₂CH═CH₂ 1-927 F F H SO₂OCH₂CH═CH₂ 1-928 F Cl H SO₂OCH₂CH═CH₂ 1-929 Cl F H SO₂OCH₂CH═CH₂ 1-930 Cl Cl H SO₂OCH₂CH═CH₂ 1-931 H F H SO₂N(CH₃)₂ 1-932 H Cl H SO₂N(CH₃)₂ 1-933 F F H SO₂N(CH₃)₂ 1-934 F Cl H SO₂N(CH₃)₂ 1-935 Cl F H SO₂N(CH₃)₂ 1-936 Cl Cl H SO₂N(CH₃)₂ 1-937 H F H SO₂N(C₂H₅)₂ 1-938 H Cl H SO₂N(C₂H₅)₂ 1-939 F F H SO₂N(C₂H₅)₂ 1-940 F Cl H SO₂N(C₂H₅)₂ 1-941 Cl F H SO₂N(C₂H₅)₂ 1-942 Cl Cl H SO₂N(C₂H₅)₂ 1-943 H F H COOH 1-944 H Cl H COOH 1-945 F F H COOH 1-946 F Cl H COOH 1-947 Cl F H COOH 1-948 Cl Cl H COOH 1-949 H F H COOCH₃ 1-950 H Cl H COOCH₃

TABLE 39 X Y R¹ B 1-951 F F H COOCH₃ 1-952 F Cl H COOCH₃ 1-953 Cl F H COOCH₃ 1-954 Cl Cl H COOCH₃ 1-955 H F H COOC₂H₅ 1-956 H Cl H COOC₂H₅ 1-957 F F H COOC₂H₅ 1-958 F Cl H COOC₂H₅ 1-959 Cl F H COOC₂H₅ 1-960 Cl Cl H COOC₂H₅ 1-961 H F H COOnC₃H₇ 1-962 H Cl H COOnC₃H₇ 1-963 F F H COOnC₃H₇ 1-964 F Cl H COOnC₃H₇ 1-965 Cl F H COOnC₃H₇ 1-966 Cl Cl H COOnC₃H₇ 1-967 H F H COOnC₄H₉ 1-968 H Cl H COOnC₄H₉ 1-969 F F H COOnC₄H₉ 1-970 F Cl H COOnC₄H₉ 1-971 Cl F H COOnC₄H₉ 1-972 Cl Cl H COOnC₄H₉ 1-973 H F H COOnC₅H₁₁ 1-974 H Cl H COOnC₅H₁₁ 1-975 F F H COOnC₅H₁₁

TABLE 40 X Y R¹ B 1-976 F Cl H COOnC₅H₁₁ 1-977 Cl F H COOnC₅H₁₁ 1-978 Cl Cl H COOnC₅H₁₁ 1-979 H F H COOiC₃H₇ 1-980 H Cl H COOiC₃H₇ 1-981 F F H COOiC₃H₇ 1-982 F Cl H COOiC₃H₇ 1-983 Cl F H COOiC₃H₇ 1-984 Cl Cl H COOiC₃H₇ 1-985 H F H COOcC₅H₉ 1-986 H Cl H COOcC₅H₉ 1-987 F F H COOcC₅H₉ 1-988 F Cl H COOcC₅H₉ 1-989 Cl F H COOcC₅H₉ 1-990 Cl Cl H COOcC₅H₉ 1-991 H F H COOcC₆H₁₁ 1-992 H Cl H COOcC₆H₁₁ 1-993 F F H COOcC₆H₁₁ 1-994 F Cl H COOcC₆H₁₁ 1-995 Cl F H COOcC₆H₁₁ 1-996 Cl Cl H COOcC₆H₁₁ 1-997 H F H COOCH₂C₆H₅ 1-998 H Cl H COOCH₂C₆H₅ 1-999 F F H COOCH₂C₆H₅ 1-1000 F Cl H COOCH₂C₆H₅

TABLE 41 X Y R¹ B 1-1001 Cl F H COOCH₂C₆H₅ 1-1002 Cl Cl H COOCH₂C₆H₅ 1-1003 H F H COOCH₂CH₂Cl 1-1004 H Cl H COOCH₂CH₂Cl 1-1005 F F H COOCH₂CH₂Cl 1-1006 F Cl H COOCH₂CH₂Cl 1-1007 Cl F H COOCH₂CH₂Cl 1-1008 Cl Cl H COOCH₂CH₂Cl 1-1009 H F H COOCH₂CH₂Br 1-1010 H Cl H COOCH₂CH₂Br 1-1011 F F H COOCH₂CH₂Br 1-1012 F Cl H COOCH₂CH₂Br 1-1013 Cl F H COOCH₂CH₂Br 1-1014 Cl Cl H COOCH₂CH₂Br 1-1015 H F H CONH₂ 1-1016 H Cl H CONH₂ 1-1017 F F H CONH₂ 1-1018 F Cl H CONH₂ 1-1019 Cl F H CONH₂ 1-1020 Cl Cl H CONH₂ 1-1021 H F H CONHCH₃ 1-1022 H Cl H CONHCH₃ 1-1023 F F H CONHCH₃ 1-1024 F Cl H CONHCH₃ 1-1025 Cl F H CONHCH₃

TABLE 42 X Y R¹ B 1-1026 Cl Cl H CONHCH₃ 1-1027 H F H CONHC₂H₅ 1-1028 H Cl H CONHC₂H₅ 1-1029 F F H CONHC₂H₅ 1-1030 F Cl H CONHC₂H₅ 1-1031 Cl F H CONHC₂H₅ 1-1032 Cl Cl H CONHC₂H₅ 1-1033 H F H CON(CH₃)₂ 1-1034 H Cl H CON(CH₃)₂ 1-1035 F F H CON(CH₃)₂ 1-1036 F Cl H CON(CH₃)₂ 1-1037 Cl F H CON(CH₃)₂ 1-1038 Cl Cl H CON(CH₃)₂ 1-1039 H F H CON(C₂H₅)₂ 1-1040 H Cl H CON(C₂H₅)₂ 1-1041 F F H CON(C₂H₅)₂ 1-1042 F Cl H CON(C₂H₅)₂ 1-1043 Cl F H CON(C₂H₅)₂ 1-1044 Cl Cl H CON(C₂H₅)₂ 1-1045 H F H CON(CH₃)(C₂H₅) 1-1046 H Cl H CON(CH₃)(C₂H₅) 1-1047 F F H CON(CH₃)(C₂H₅) 1-1048 F Cl H CON(CH₃)(C₂H₅) 1-1049 Cl F H CON(CH₃)(C₂H₅) 1-1050 Cl Cl H CON(CH₃)(C₂H₅)

TABLE 43 X Y R¹ B 1-1051 H F H COCH₃ 1-1052 H Cl 11 COCH₃ 1-1053 F F H COCH₃ 1-1054 F Cl H COCH₃ 1-1055 Cl F H COCH₃ 1-1056 Cl Cl H COCH₃ 1-1057 H F H COC₂H₅ 1-1058 H Cl H COC₂H₅ 1-1059 F F H COC₂H₅ 1-1060 F Cl H COC₂H₅ 1-1061 Cl F H COC₂H₅ 1-1062 Cl Cl H COC₂H₅ 1-1063 H F H COCH₂Cl 1-1064 H Cl H COCH₂Cl 1-1065 F F H COCH₂Cl 1-1066 F Cl H COCH₂Cl 1-1067 Cl F H COCH₂Cl 1-1068 Cl Cl H COCH₂Cl 1-1069 H F H CHO 1-1070 H Cl H CHO 1-1071 F F H CHO 1-1072 F Cl H CHO 1-1073 Cl F H CHO 1-1074 Cl Cl H CHO 1-1075 H F H CH₂CH₂COOH

TABLE 44 X Y R¹ B 1-1076 H Cl H CH₂CH₂COOH 1-1077 F F H CH₂CH₂COOH 1-1078 F Cl H CH₂CH₂COOH 1-1079 Cl F H CH₂CH₂COOH 1-1080 Cl Cl H CH₂CH₂COOH 1-1081 H F H CH₂CH₂COOCH₃ 1-1082 H Cl H CH₂CH₂COOCH₃ 1-1083 F F H CH₂CH₂COOCH₃ 1-1084 F Cl H CH₂CH₂COOCH₃ 1-1085 Cl F H CH₂CH₂COOCH₃ 1-1086 Cl Cl H CH₂CH₂COOCH₃ 1-1087 H F H CH₂CH₂COOC₂H₅ 1-1088 H Cl H CH₂CH₂COOC₂H₅ 1-1089 F F H CH₂CH₂COOC₂H₅ 1-1090 F Cl H CH₂CH₂COOC₂H₅ 1-1091 Cl F H CH₂CH₂COOC₂H₅ 1-1092 Cl Cl H CH₂CH₂COOC₂H₅ 1-1093 H F H CH₂CHClCOOCH₃ 1-1094 H Cl H CH₂CHClCOOCH₃ 1-1095 F F H CH₂CHClCOOCH₃ 1-1096 F Cl H CH₂CHClCOOCH₃ 1-1097 Cl F H CH₂CHClCOOCH₃ 1-1098 Cl Cl H CH₂CHClCOOCH₃ 1-1099 H F H CH₂CHClCOOC₂H₅ 1-1100 H Cl H CH₂CHClCOOC₂H₅

TABLE 45 X Y R¹ B 1-1101 F F H CH₂CHClCOOC₂H₅ 1-1102 F Cl H CH₂CHClCOOC₂H₅ 1-1103 Cl F H CH₂CHClCOOC₂H₅ 1-1104 Cl Cl H CH₂CHClCOOC₂H₅ 1-1105 H F H CH═CHCOOCH₃ 1-1106 H Cl H CH═CHCOOCH₃ 1-1107 F F H CH═CHCOOCH₃ 1-1108 F Cl H CH═CHCOOCH₃ 1-1109 Cl F H CH═CHCOOCH₃ 1-1110 Cl Cl H CH═CHCOOCH₃ 1-1111 H F H CH═CHCOOC₂H₅ 1-1112 H Cl H CH═CHCOOC₂H₅ 1-1113 F F H CH═CHCOOC₂H₅ 1-1114 F Cl H CH═CHCOOC₂H₅ 1-1115 Cl F H CH═CHCOOC₂H₅ 1-1116 Cl Cl H CH═CHCOOC₂H₅ 1-1117 H F H C(CH₃)═NOH 1-1118 H Cl H C(CH₃)═NOH 1-1119 F F H C(CH₃)═NOH 1-1120 F Cl H C(CH₃)═NOH 1-1121 Cl F H C(CH₃)═NOH 1-1122 Cl Cl H C(CH₃)═NOH 1-1123 H F H C(CH₃)═NOCH₃ 1-1124 H Cl H C(CH₃)═NOCH₃ 1-1125 F F H C(CH₃)═NOCH₃

TABLE 46 X Y R¹ B 1-1126 F Cl H C(CH₃)═NOCH₃ 1-1127 Cl F H C(CH₃)═NOCH₃ 1-1128 Cl Cl H C(CH₃)═NOCH₃ 1-1129 H F H C(CH₃)═NOC₂H₅ 1-1130 H Cl H C(CH₃)═NOC₂H₅ 1-1131 F F H C(CH₃)═NOC₂H₅ 1-1132 F Cl H C(CH₃)═NOC₂H₅ 1-1133 Cl F H C(CH₃)═NOC₂H₅ 1-1134 Cl Cl H C(CH₃)═NOC₂H₅ 1-1135 H F H C(CH₃)═NOiC₃H₇ 1-1136 H Cl H C(CH₃)═NOiC₃H₇ 1-1137 F F H C(CH₃)═NOiC₃H₇ 1-1138 F Cl H C(CH₃)═NOiC₃H₇ 1-1139 Cl F H C(CH₃)═NOiC₃H₇ 1-1140 Cl Cl H C(CH₃)═NOiC₃H₇ 1-1141 H F H C(CH₃)═NNH₂ 1-1142 H Cl H C(CH₃)═NNH₂ 1-1143 F F H C(CH₃)═NNH₂ 1-1144 F Cl H C(CH₃)═NNH₂ 1-1145 Cl F H C(CH₃)═NNH₂ 1-1146 Cl Cl H C(CH₃)═NNH₂ 1-1147 H F H C(CH₃)═NNHCH₃ 1-1148 H Cl H C(CH₃)═NNHCH₃ 1-1149 F F H C(CH₃)═NNHCH₃ 1-1150 F Cl H C(CH₃)═NNHCH₃

TABLE 47 X Y R¹ B 1-1151 Cl F H C(CH₃)═NNHCH₃ 1-1152 Cl Cl H C(CH₃)═NNHCH₃ 1-1153 H F H C(CH₃)═NN(CH₃)₂ 1-1154 H Cl H C(CH₃)═NN(CH₃)₂ 1-1155 F F H C(CH₃)═NN(CH₃)₂ 1-1156 F Cl H C(CH₃)═NN(CH₃)₂ 1-1157 Cl F H C(CH₃)═NN(CH₃)₂ 1-1158 Cl Cl H C(CH₃)═NN(CH₃)₂ 1-1159 H F H C(CH₃)═NNHC₂H₅ 1-1160 H Cl H C(CH₃)═NNHC₂H₅ 1-1161 F F H C(CH₃)═NNHC₂H₅ 1-1162 F Cl H C(CH₃)═NNHC₂H₅ 1-1163 Cl F H C(CH₃)═NNHC₂H₅ 1-1164 Cl Cl H C(CH₃)═NNHC₂H₅ 1-1165 H F H C(CH₃)═NN(C₂H₅)₂ 1-1166 H Cl H C(CH₃)═NN(C₂H₅)₂ 1-1167 F F H C(CH₃)═NN(C₂H₅)₂ 1-1168 F Cl H C(CH₃)═NN(C₂H₅)₂ 1-1169 Cl F H C(CH₃)═NN(C₂H₅)₂ 1-1170 Cl Cl H C(CH₃)═NN(C₂H₅)₂ 1-1171 H F H C(C₂H₅)═NNH₂ 1-1172 H Cl H C(C₂H₅)═NNH₂ 1-1173 F F H C(C₂H₅)═NNH₂ 1-1174 F Cl H C(C₂H₅)═NNH₂ 1-1175 Cl F H C(C₂H₅)═NNH₂

TABLE 48 X Y R¹ B 1-1176 Cl Cl H C(C₂H₅)═NNH₂ 1-1177 H F H C(C₂H₅)═NNHCH₃ 1-1178 H Cl H C(C₂H₅)═NNHCH₃ 1-1179 F F H C(C₂H₅)═NNHCH₃ 1-1180 F Cl H C(C₂H₅)═NNHCH₃ 1-1181 Cl F H C(C₂H₅)═NNHCH₃ 1-1182 Cl Cl H C(C₂H₅)═NNHCH₃ 1-1183 H F H C(C₂H₅)═NN(CH₃)₂ 1-1184 H Cl H C(C₂H₅)═NN(CH₃)₂ 1-1185 F F H C(C₂H₅)═NN(CH₃)₂ 1-1186 F Cl H C(C₂H₅)═NN(CH₃)₂ 1-1187 Cl F H C(C₂H₅)═NN(CH₃)₂ 1-1188 Cl Cl H C(C₂H₅)═NN(CH₃)₂ 1-1189 H F H C(C₂H₅)═NNHC₂H₅ 1-1190 H Cl H C(C₂H₅)═NNHC₂H₅ 1-1191 F F H C(C₂H₅)═NNHC₂H₅ 1-1192 F Cl H C(C₂H₅)═NNHC₂H₅ 1-1193 Cl F H C(C₂H₅)═NNHC₂H₅ 1-1194 Cl Cl H C(C₂H₅)═NNHC₂H₅ 1-1195 H F H C(C₂H₅)═NN(C₂H₅)₂ 1-1196 H Cl H C(C₂H₅)═NN(C₂H₅)₂ 1-1197 F F H C(C₂H₅)═NN(C₂H₅)₂ 1-1198 F Cl H C(C₂H₅)═NN(C₂H₅)₂ 1-1199 Cl F H C(C₂H₅)═NN(C₂H₅)₂ 1-1200 Cl Cl H C(C₂H₅)═NN(C₂H₅)₂

TABLE 49 X Y R¹ B 1-1201 H F H C(CH₃)(OCH₃)₂ 1-1202 H Cl H C(CH₃)(OCH₃)₂ 1-1203 F F H C(CH₃)(OCH₃)₂ 1-1204 F Cl H C(CH₃)(OCH₃)₂ 1-1205 Cl F H C(CH₃)(OCH₃)₂ 1-1206 Cl Cl H C(CH₃)(OCH₃)₂ 1-1207 H F H C(CH₃)(OC₂H₅)₂ 1-1208 H Cl H C(CH₃)(OC₂H₅)₂ 1-1209 F F H C(CH₃)(OC₂H₅)₂ 1-1210 F Cl H C(CH₃)(OC₂H₅)₂ 1-1211 Cl F H C(CH₃)(OC₂H₅)₂ 1-1212 Cl Cl H C(CH₃)(OC₂H₅)₂ 1-1213 H F H C(CH₃)(OiC₃H₇)₂ 1-1214 H Cl H C(CH₃)(OiC₃H₇)₂ 1-1215 F F H C(CH₃)(OiC₃H₇)₂ 1-1216 F Cl H C(CH₃)(OiC₃H₇)₂ 1-1217 Cl F H C(CH₃)(OiC₃H₇)₂ 1-1218 Cl Cl H C(CH₃)(OiC₃H₇)₂ 1-1219 H F H C(CH₃)(OCH₂CH₂O) 1-1220 H Cl H C(CH₃)(OCH₂CH₂O) 1-1221 F F H C(CH₃)(OCH₂CH₂O) 1-1222 F Cl H C(CH₃)(OCH₂CH₂O) 1-1223 Cl F H C(CH₃)(OCH₂CH₂O) 1-1224 Cl Cl H C(CH₃)(OCH₂CH₂O) 1-1225 H F H C(CH₃)(OCH₂CH₂CH₂O)

TABLE 50 X Y R¹ B 1-1226 H Cl H C(CH₃)(OCH₂CH₂CH₂O) 1-1227 F F H C(CH₃)(OCH₂CH₂CH₂O) 1-1228 F Cl H C(CH₃)(OCH₂CH₂CH₂O) 1-1229 Cl F H C(CH₃)(OCH₂CH₂CH₂O) 1-1230 Cl Cl H C(CH₃)(OCH₂CH₂CH₂O) 1-1231 H F H C(C₂H₅)(OCH₂CH₂O) 1-1232 H Cl H C(C₂H₅)(OCH₂CH₂O) 1-1233 F F H C(C₂H₅)(OCH₂CH₂O) 1-1234 F Cl H C(C₂H₅)(OCH₂CH₂O) 1-1235 Cl F H C(C₂H₅)(OCH₂CH₂O) 1-1236 Cl Cl H C(C₂H₅)(OCH₂CH₂O) 1-1237 H F H C(C₂H₅)(OCH₂CH₂CH₂O) 1-1238 H Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 1-1239 F F H C(C₂H₅)(OCH₂CH₂CH₂O) 1-1240 F Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 1-1241 Cl F H C(C₂H₅)(OCH₂CH₂CH₂O) 1-1242 Cl Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 1-1243 H F H OCH₂CH(CH₃)₂ 1-1244 H Cl H OCH₂CH(CH₃)₂ 1-1245 F F H OCH₂CH(CH₃)₂ 1-1246 F Cl H OCH₂CH(CH₃)₂ 1-1247 Cl F H OCH₂CH(CH₃)₂ 1-1248 Cl Cl H OCH₂CH(CH₃)₂ 1-1249 H F H OCH₂CH₂F 1-1250 H Cl H OCH₂CH₂F

TABLE 51 X Y R¹ B 1-1251 F F H OCH₂CH₂F 1-1252 F Cl H OCH₂CH₂F 1-1253 Cl F H OCH₂CH₂F 1-1254 Cl Cl H OCH₂CH₂F 1-1255 H Cl H CH₂OH 1-1256 F Cl H CH₂OH 1-1257 H Cl H CH₂OCOCH₃ 1-1258 F Cl H CH₂OCOCH₃

Compounds of the general formula:

TABLE 52 X Z¹ n R¹ R⁴ R⁵ 2-1 H O 1 H H H 2-2 F O 1 H H H 2-3 H O 1 H H CH₃ 2-4 F O 1 H H CH₃ 2-5 H O 1 H H C₂H₅ 2-6 F O 1 H H C₂H₅ 2-7 H O 1 H H nC₃H₇ 2-8 F O 1 H H nC₃H₇ 2-9 H O 1 H H nC₄H₉ 2-10 F O 1 H H nC₄H₉ 2-11 H O 1 H H nC₅H₁₁ 2-12 F O 1 H H nC₅H₁₁ 2-13 H O 1 H H iC₃H₇ 2-14 F O 1 H H iC₃H₇ 2-15 H O 1 H H CH₂CH₂Cl 2-16 F O 1 H H CH₂CH₂Cl 2-17 H O 1 H H CH₂CH₂Br 2-18 F O 1 H H CH₂CH₂Br 2-19 H O 1 H H CH₂CH═CH₂ 2-20 F O 1 H H CH₂CH═CH₂ 2-21 H O 1 H H CH(CH₃)CH═CH₂ 2-22 F O 1 H H CH(CH₃)CH═CH₂ 2-23 H O 1 H H CH₂CCl═CH₂ 2-24 F O 1 H H CH₂CCl═CH₂ 2-25 H O 1 H H CH₂C≡CH

TABLE 53 X Z¹ n R¹ R⁴ R⁵ 2-26 F O 1 H H CH₂C≡CH 2-27 H O 1 H H CH(CH₃)C≡CH 2-28 F O 1 H H CH(CH₃)C≡CH 2-29 H O 1 H H CH₂CN 2-30 F O 1 H H CH₂CN 2-31 H O 1 H H CH₂OCH₃ 2-32 F O 1 H H CH₂OCH₃ 2-33 H O 1 H H CH₂OC₂H₅ 2-34 F O 1 H H CH₂OC₂H₅ 2-35 H O 1 H H CH₂COOH 2-36 F O 1 H H CH₂COOH 2-37 H O 1 H H CH₂COOCH₃ 2-38 F O 1 H H CH₂COOCH₃ 2-39 H O 1 H H CH₂COOC₂H₅ 2-40 F O 1 H H CH₂COOC₂H₅ 2-41 H O 1 H H CH₂COOnC₃H₇ 2-42 F O 1 H H CH₂COOnC₃H₇ 2-43 H O 1 H H CH₂COOnC₄H₉ 2-44 F O 1 H H CH₂COOnC₄H₉ 2-45 H O 1 H H CH₂COOnC₅H₁₁ 2-46 F O 1 H H CH₂COOnC₅H₁₁ 2-47 H O 1 H H CH₂COOiC₃H₇ 2-48 F O 1 H H CH₂COOiC₃H₇ 2-49 H O 1 H H CH₂COOcC₅H₉ 2-50 F O 1 H H CH₂COOcC₅H₉

TABLE 54 X Z¹ n R¹ R⁴ R⁵ 2-51 H O 1 H H CH₂COOcC₆H₁₁ 2-52 F O 1 H H CH₂COOcC₆H₁₁ 2-53 H O 1 H H CH(CH₃)COOH 2-54 F O 1 H H CH(CH₃)COOH 2-55 H O 1 H H CH(CH₃)COOCH₃ 2-56 F O 1 H H CH(CH₃)COOCH₃ 2-57 H O 1 H H CH(CH₃)COOC₂H₅ 2-58 F O 1 H H CH(CH₃)COOC₂H₅ 2-59 H O 1 H H CH(CH₃)COOnC₃H₇ 2-60 F O 1 H H CH(CH₃)COOnC₃H₇ 2-61 H O 1 H H CH(CH₃)COOnC₄H₉ 2-62 F O 1 H H CH(CH₃)COOnC₄H₉ 2-63 H O 1 H H CH(CH₃)COOnC₅H₁₁ 2-64 F O 1 H H CH(CH₃)COOnC₅H₁₁ 2-65 H O 1 H H CH(CH₃)COOiC₃H₇ 2-66 F O 1 H H CH(CH₃)COOiC₃H₇ 2-67 H O 1 H H CH(CH₃)COOcC₅H₉ 2-68 F O 1 H H CH(CH₃)COOcC₅H₉ 2-69 H O 1 H H CH(CH₃)COOcC₆H₁₁ 2-70 F O 1 H H CH(CH₃)COOcC₆H₁₁ 2-71 H O 1 H CH₃ H 2-72 F O 1 H CH₃ H 2-73 H O 1 H CH₃ CH₃ 2-74 F O 1 H CH₃ CH₃ 2-75 H O 1 H CH₃ C₂H₅

TABLE 55 X Z¹ n R¹ R⁴ R⁵ 2-76 F O 1 H CH₃ C₂H₅ 2-77 H O 1 H CH₃ nC₃H₇ 2-78 F O 1 H CH₃ nC₃H₇ 2-79 H O 1 H CH₃ nC₄H₉ 2-80 F O 1 H CH₃ nC₄H₉ 2-81 H O 1 H CH₃ nC₅H₁₁ 2-82 F O 1 H CH₃ nC₅H₁₁ 2-83 H O 1 H CH₃ iC₃H₇ 2-84 F O 1 H CH₃ iC₃H₇ 2-85 H O 1 H CH₃ CH₂CH₂Cl 2-86 F O 1 H CH₃ CH₂CH₂Cl 2-87 H O 1 H CH₃ CH₂CH₂Br 2-88 F O 1 H CH₃ CH₂CH₂Br 2-89 H O 1 H CH₃ CH₂CH═CH₂ 2-90 F O 1 H CH₃ CH₂CH═CH₂ 2-91 H O 1 H CH₃ CH(CH₃)CH═CH₂ 2-92 F O 1 H CH₃ CH(CH₃)CH═CH₂ 2-93 H O 1 H CH₃ CH₂CCl═CH₂ 2-94 F O 1 H CH₃ CH₂CCl═CH₂ 2-95 H O 1 H CH₃ CH₂C≡CH 2-96 F O 1 H CH₃ CH₂C≡CH 2-97 H O 1 H CH₃ CH(CH₃)C≡CH 2-98 F O 1 H CH₃ CH(CH₃)C≡CH 2-99 H O 1 H CH₃ CH₂CN  2-100 F O 1 H CH₃ CH₂CN

TABLE 56 X Z¹ n R¹ R⁴ R⁵ 2-101 H O 1 H CH₃ CH₂OCH₃ 2-102 F O 1 H CH₃ CH₂OCH₃ 2-103 H O 1 H CH₃ CH₂OC₂H₅ 2-104 F O 1 H CH₃ CH₂OC₂H₅ 2-105 H O 0 H — H 2-106 F O 0 H — H 2-107 H O 0 H — CH₃ 2-108 F O 0 H — CH₃ 2-109 H O 0 H — C₂H₅ 2-110 F O 0 H — C₂H₅ 2-111 H O 0 H — nC₃H₇ 2-112 F O 0 H — nC₃H₇ 2-113 H O 0 H — nC₄H₉ 2-114 F O 0 H — nC₄H₉ 2-115 H O 0 H — nC₅H₁₁ 2-116 F O 0 H — nC₅H₁₁ 2-117 H O 0 H — iC₃H₇ 2-118 F O 0 H — iC₃H₇ 2-119 H O 0 H — CH₂CH₂Cl 2-120 F O 0 H — CH₂CH₂Cl 2-121 H O 0 H — CH₂CH₂Br 2-122 F O 0 H — CH₂CH₂Br 2-123 H O 0 H — CH₂CH═CH₂ 2-124 F O 0 H — CH₂CH═CH₂ 2-125 H O 0 H — CH(CH₃)CH═CH₂

TABLE 57 X Z¹ n R¹ R⁴ R⁵ 2-126 F O 0 H — CH(CH₃)CH═CH₂ 2-127 H O 0 H — CH₂CCl═CH₂ 2-128 F O 0 H — CH₂CCl═CH₂ 2-129 H O 0 H — CH₂C≡CH 2-130 F O 0 H — CH₂C≡CH 2-131 H O 0 H — CH(CH₃)C≡CH 2-132 F O 0 H — CH(CH₃)C≡CH 2-133 H O 0 H — CH₂CN 2-134 F O 0 H — CH₂CN 2-135 H O 0 H — CH₂OCH₃ 2-136 F O 0 H — CH₂OCH₃ 2-137 H O 0 H — CH₂OC₂H₅ 2-138 F O 0 H — CH₂OC₂H₅ 2-139 H S 0 H — H 2-140 F S 0 H — H 2-141 H S 0 H — CH₃ 2-142 F S 0 H — CH₃ 2-143 H S 0 H — C₂H₅ 2-144 F S 0 H — C₂H₅ 2-145 H S 0 H — nC₃H₇ 2-146 F S 0 H — nC₃H₇ 2-147 H S 0 H — nC₄H₉ 2-148 F S 0 H — nC₄H₉ 2-149 H S 0 H — nC₅H₁₁ 2-150 F S 0 H — nC₅H₁₁

TABLE 58 X Z¹ n R¹ R⁴ R⁵ 2-151 H S 0 H — iC₃H₇ 2-152 F S 0 H — iC₃H₇ 2-153 H S 0 H — CH₂CH₂Cl 2-154 F S 0 H — CH₂CH₂Cl 2-155 H S 0 H — CH₂CH₂Br 2-156 F S 0 H — CH₂CH₂Br 2-157 H S 0 H — CH₂CH═CH₂ 2-158 F S 0 H — CH₂CH═CH₂ 2-159 H S 0 H — CH(CH₃)CH═CH₂ 2-160 F S 0 H — CH(CH₃)CH═CH₂ 2-161 H S 0 H — CH₂CCl═CH₂ 2-162 F S 0 H — CH₂CCl═CH₂ 2-163 H S 0 H — CH₂C≡CH 2-164 F S 0 H — CH₂C≡CH 2-165 H S 0 H — CH(CH₃)C≡CH 2-166 F S 0 H — CH(CH₃)C≡CH 2-167 H S 0 H — CH₂CN 2-168 F S 0 H — CH₂CN 2-169 H S 0 H — CH₂OCH₃ 2-170 F S 0 H — CH₂OCH₃ 2-171 H S 0 H — CH₂OC₂H₅ 2-172 F S 0 H — CH₂OC₂H₅ 2-173 H S 0 H — CH₂COOH 2-174 F S 0 H — CH₂COOH 2-175 H S 0 H — CH₂COOCH₃

TABLE 59 X Z¹ n R¹ R⁴ R⁵ 2-176 F S 0 H — CH₂COOCH₃ 2-177 H S 0 H — CH₂COOC₂H₅ 2-178 F S 0 H — CH₂COOC₂H₅ 2-179 H S 0 H — CH₂COOnC₃H₇ 2-180 F S 0 H — CH₂COOnC₃H₇ 2-181 H S 0 H — CH₂COOnC₄H₉ 2-182 F S 0 H — CH₂COOnC₄H₉ 2-183 H S 0 H — CH₂COOnC₅H₁₁ 2-184 F S 0 H — CH₂COOnC₅H₁₁ 2-185 H S 0 H — CH₂COOiC₃H₇ 2-186 F S 0 H — CH₂COOiC₃H₇ 2-187 H S 0 H — CH₂COOcC₅H₉ 2-188 F S 0 H — CH₂COOcC₅H₉ 2-189 H S 0 H — CH₂COOcC₆H₁₁ 2-190 F S 0 H — CH₂COOcC₆H₁₁ 2-191 H S 0 H — CH(CH₃)COOH 2-192 F S 0 H — CH(CH₃)COOH 2-193 H S 0 H — CH(CH₃)COOCH₃ 2-194 F S 0 H — CH(CH₃)COOCH₃ 2-195 H S 0 H — CH(CH₃)COOC₂H₅ 2-196 F S 0 H — CH(CH₃)COOC₂H₅ 2-197 H S 0 H — CH(CH₃)COOnC₃H₇ 2-198 F S 0 H — CH(CH₃)COOnC₃H₇ 2-199 H S 0 H — CH(CH₃)COOnC₄H₉ 2-200 F S 0 H — CH(CH₃)COOnC₄H₉

TABLE 60 X Z¹ n R¹ R⁴ R⁵ 2-201 H S 0 H — CH(CH₃)COOnC₅H₁₁ 2-202 F S 0 H — CH(CH₃)COOnC₅H₁₁ 2-203 H S 0 H — CH(CH₃)COOiC₃H₇ 2-204 F S 0 H — CH(CH₃)COOiC₃H₇ 2-205 H S 0 H — CH(CH₃)COOcC₅H₉ 2-206 F S 0 H — CH(CH₃)COOcC₅H₉ 2-207 H S 0 H — CH(CH₃)COOcC₆H₁₁ 2-208 F S 0 H — CH(CH₃)COOcC₆H₁₁

Compounds of the general formula:

TABLE 61 X R¹ R⁵ 5-1  H H CH₃ 5-2  F H CH₃ 5-3  Cl H CH₃ 5-4  H H C₂H₅ 5-5  F H C₂H₅ 5-6  Cl H C₂H₅ 5-7  H H nC₃H₇ 5-8  F H nC₃H₇ 5-9  Cl H nC₃H₇ 5-10 H H nC₄H₉ 5-11 F H nC₄H₉ 5-12 Cl H nC₄H₉ 5-13 H H iC₄H₉ 5-14 F H iC₄H₉ 5-15 Cl H iC₄H₉ 5-16 H H CH₂CH═CH₂ 5-17 F H CH₂CH═CH₂ 5-18 Cl H CH₂CH═CH₂ 5-19 H H CH(CH₃)CH═CH₂ 5-20 F H CH(CH₃)CH═CH₂ 5-21 Cl H CH(CH₃)CH═CH₂ 5-22 H H CH₂C≡CH 5-23 F H CH₂C≡CH 5-24 Cl H CH₂C≡CH 5-25 H H CH(CH₃)C≡CH

TABLE 62 X R¹ R⁵ 5-26 F H CH(CH₃)C≡CH 5-27 Cl H CH(CH₃)C≡CH

Compounds of the general formula:

TABLE 63 X Y R¹ B 6-1  H F H H 6-2  H Cl H H 6-3  H Br H H 6-4  F F H H 6-5  F Cl H H 6-6  F Br H H 6-7  Cl F H H 6-8  Cl Cl H H 6-9  Cl Br H H 6-10 H F H NO₂ 6-11 H Cl H NO₂ 6-12 H Br H NO₂ 6-13 F F H NO₂ 6-14 F Cl H NO₂ 6-15 F Br H NO₂ 6-16 Cl F H NO₂ 6-17 Cl Cl H NO₂ 6-18 Cl Br H NO₂ 6-19 H F H NH₂ 6-20 H Cl H NH₂ 6-21 H Br H NH₂ 6-22 F F H NH₂ 6-23 F Cl H NH₂ 6-24 F Br H NH₂ 6-25 Cl F H NH₂

TABLE 64 X Y R¹ B 6-26 Cl Cl H NH₂ 6-27 Cl Br H NH₂ 6-28 H F H OH 6-29 H Cl H OH 6-30 H Br H OH 6-31 F F H OH 6-32 F Cl H OH 6-33 F Br H OH 6-34 Cl F H OH 6-35 Cl Cl H OH 6-36 Cl Br H OH 6-37 H F H SH 6-38 H Cl H SH 6-39 H Br H SH 6-40 F F H SH 6-41 F Cl H SH 6-42 F Br H SH 6-43 Cl F H SH 6-44 Cl Cl H SH 6-45 Cl Br H SH 6-46 H F H SO₂Cl 6-47 H Cl H SO₂Cl 6-48 H Br H SO₂Cl 6-49 F F H SO₂Cl 6-50 F Cl H SO₂Cl

TABLE 65 X Y R¹ B 6-51 F Br H SO₂Cl 6-52 Cl F H SO₂Cl 6-53 Cl Cl H SO₂Cl 6-54 Cl Br H SO₂Cl 6-55 H F H NHCH₃ 6-56 H Cl H NHCH₃ 6-57 F F H NHCH₃ 6-58 F Cl H NHCH₃ 6-59 Cl F H NHCH₃ 6-60 Cl Cl H NHCH₃ 6-61 H F H NHC₂H₅ 6-62 H Cl H NHC₂H₅ 6-63 F F H NHC₂H₅ 6-64 F Cl H NHC₂H₅ 6-65 Cl F H NHC₂H₅ 6-66 Cl Cl H NHC₂H₅ 6-67 H F H NHCH₂CH═CH₂ 6-68 H Cl H NHCH₂CH═CH₂ 6-69 F F H NHCH₂CH═CH₂ 6-70 F Cl H NHCH₂CH═CH₂ 6-71 Cl F H NHCH₂CH═CH₂ 6-72 Cl Cl H NHCH₂CH═CH₂ 6-73 H F H NHCH₂C≡CH 6-74 H Cl H NHCH₂C≡CH 6-75 F F H NHCH₂C≡CH

TABLE 66 X Y R¹ B 6-76 F Cl H NHCH₂C≡CH 6-77 Cl F H NHCH₂C≡CH 6-78 Cl Cl H NHCH₂C≡CH 6-79 H F H NHCH(CH₃)C≡CH 6-80 H Cl H NHCH(CH₃)C≡CH 6-81 F F H NHCH(CH₃)C≡CH 6-82 F Cl H NHCH(CH₃)C≡CH 6-83 Cl F H NHCH(CH₃)C≡CH 6-84 Cl Cl H NHCH(CH₃)C≡CH 6-85 H F H NHSO₂CH₃ 6-86 H Cl H NHSO₂CH₃ 6-87 F F H NHSO₂CH₃ 6-88 F Cl H NHSO₂CH₃ 6-89 Cl F H NHSO₂CH₃ 6-90 Cl Cl H NHSO₂CH₃ 6-91 H F H NHSO₂C₂H₅ 6-92 H Cl H NHSO₂C₂H₅ 6-93 F F H NHSO₂C₂H₅ 6-94 F Cl H NHSO₂C₂H₅ 6-95 Cl F H NHSO₂C₂H₅ 6-96 Cl Cl H NHSO₂C₂H₅ 6-97 H F H NHSO₂CH₂Cl 6-98 H Cl H NHSO₂CH₂Cl 6-99 F F H NHSO₂CH₂Cl  6-100 F Cl H NHSO₂CH₂Cl

TABLE 67 X Y R¹ B 6-101 Cl F H NHSO₂CH₂Cl 6-102 Cl Cl H NHSO₂CH₂Cl 6-103 H F H NHSO₂CF₃ 6-104 H Cl H NHSO₂CF₃ 6-105 F F H NHSO₂CF₃ 6-106 F Cl H NHSO₂CF₃ 6-107 Cl F H NHSO₂CF₃ 6-108 Cl Cl H NHSO₂CF₃ 6-109 H F H N(SO₂CH₃)₂ 6-110 H Cl H N(SO₂CH₃)₂ 6-111 F F H N(SO₂CH₃)₂ 6-112 F Cl H N(SO₂CH₃)₂ 6-113 Cl F H N(SO₂CH₃)₂ 6-114 Cl Cl H N(SO₂CH₃)₂ 6-115 H F H N(CH₃)SO₂CH₃ 6-116 H Cl H N(CH₃)SO₂CH₃ 6-117 F F H N(CH₃)SO₂CH₃ 6-118 F Cl H N(CH₃)SO₂CH₃ 6-119 Cl F H N(CH₃)SO₂CH₃ 6-120 Cl Cl H N(CH₃)SO₂CH₃ 6-121 H F H N(CH₂C≡CH)SO₂CH₃ 6-122 H Cl H N(CH₂C≡CH)SO₂CH₃ 6-123 F F H N(CH₂C≡CH)SO₂CH₃ 6-124 F Cl H N(CH₂C≡CH)SO₂CH₃ 6-125 Cl F H N(CH₂C≡CH)SO₂CH₃

TABLE 68 X Y R¹ B 6-126 Cl Cl H N(CH₂C≡CH)SO₂CH₃ 6-127 H F H NHCOOCH₃ 6-128 H Cl H NHCOOCH₃ 6-129 F F H NHCOOCH₃ 6-130 F Cl H NHCOOCH₃ 6-131 Cl F H NHCOOCH₃ 6-132 Cl Cl H NHCOOCH₃ 6-133 H F H NHCOOC₂H₅ 6-134 H Cl H NHCOOC₂H₅ 6-135 F F H NHCOOC₂H₅ 6-136 F Cl H NHCOOC₂H₅ 6-137 Cl F H NHCOOC₂H₅ 6-138 Cl Cl H NHCOOC₂H₅ 6-139 H F H NHCOOnC₃H₇ 6-140 H Cl H NHCOOnC₃H₇ 6-141 F F H NHCOOnC₃H₇ 6-142 F Cl H NHCOOnC₃H₇ 6-143 Cl F H NHCOOnC₃H₇ 6-144 Cl Cl H NHCOOnC₃H₇ 6-145 H F H NHCOOiC₃H₇ 6-146 H Cl H NHCOOiC₃H₇ 6-147 F F H NHCOOiC₃H₇ 6-148 F Cl H NHCOOiC₃H₇ 6-149 Cl F H NHCOOiC₃H₇ 6-150 Cl Cl H NHCOOiC₃H₇

TABLE 69 X Y R¹ B 6-151 H F H NHCOOnC₄H₉ 6-152 H Cl H NHCOOnC₄H₉ 6-153 F F H NHCOOnC₄H₉ 6-154 F Cl H NHCOOnC₄H₉ 6-155 Cl F H NHCOOnC₄H₉ 6-156 Cl Cl H NHCOOnC₄H₉ 6-157 H F H NHCOOnC₅H₁₁ 6-158 H Cl H NHCOOnC₅H₁₁ 6-159 F F H NHCOOnC₅H₁₁ 6-160 F Cl H NHCOOnC₅H₁₁ 6-161 Cl F H NHCOOnC₅H₁₁ 6-162 Cl Cl H NHCOOnC₅H₁₁ 6-163 H F H NHCH₂COOCH₃ 6-164 H Cl H NHCH₂COOCH₃ 6-165 F F H NHCH₂COOCH₃ 6-166 F Cl H NHCH₂COOCH₃ 6-167 Cl F H NHCH₂COOCH₃ 6-168 Cl Cl H NHCH₂COOCH₃ 6-169 H F H NHCH₂COOC₂H₅ 6-170 H Cl H NHCH₂COOC₂H₅ 6-171 F F H NHCH₂COOC₂H₅ 6-172 F Cl H NHCH₂COOC₂H₅ 6-173 Cl F H NHCH₂COOC₂H₅ 6-174 Cl Cl H NHCH₂COOC₂H₅ 6-175 H F H NHCH₂COOnC₃H₇

TABLE 70 X Y R¹ B 6-176 H Cl H NHCH₂COOnC₃H₇ 6-177 F F H NHCH₂COOnC₃H₇ 6-178 F Cl H NHCH₂COOnC₃H₇ 6-179 Cl F H NHCH₂COOnC₃H₇ 6-180 Cl Cl H NHCH₂COOnC₃H₇ 6-181 H F H NHCH₂COOnC₄H₉ 6-182 H Cl H NHCH₂COOnC₄H₉ 6-183 F F H NHCH₂COOnC₄H₉ 6-184 F Cl H NHCH₂COOnC₄H₉ 6-185 Cl F H NHCH₂COOnC₄H₉ 6-186 Cl Cl H NHCH₂COOnC₄H₉ 6-187 H F H NHCH₂COOnC₅H₁₁ 6-188 H Cl H NHCH₂COOnC₅H₁₁ 6-189 F F H NHCH₂COOnC₅H₁₁ 6-190 F Cl H NHCH₂COOnC₅H₁₁ 6-191 Cl F H NHCH₂COOnC₅H₁₁ 6-192 Cl Cl H NHCH₂COOnC₅H₁₁ 6-193 H F H NHCH₂COOiC₃H₇ 6-194 H Cl H NHCH₂COOiC₃H₇ 6-195 F F H NHCH₂COOiC₃H₇ 6-196 F Cl H NHCH₂COOiC₃H₇ 6-197 Cl F H NHCH₂COOiC₃H₇ 6-198 Cl Cl H NHCH₂COOiC₃H₇ 6-199 H F H NHCH₂COOcC₅H₉ 6-200 H Cl H NHCH₂COOcC₅H₉

TABLE 71 X Y R¹ B 6-201 F F H NHCH₂COOcC₅H₉ 6-202 F Cl H NHCH₂COOcC₅H₉ 6-203 Cl F H NHCH₂COOcC₅H₉ 6-204 Cl Cl H NHCH₂COOcC₅H₉ 6-205 H F H NHCH₂COOcC₆H₁₁ 6-206 H Cl H NHCH₂COOcC₆H₁₁ 6-207 F F H NHCH₂COOcC₆H₁₁ 6-208 F Cl H NHCH₂COOcC₆H₁₁ 6-209 Cl F H NHCH₂COOcC₆H₁₁ 6-210 Cl Cl H NHCH₂COOcC₆H₁₁ 6-211 H F H NHCH(CH₃)COOCH₃ 6-212 H Cl H NHCH(CH₃)COOCH₃ 6-213 F F H NHCH(CH₃)COOCH₃ 6-214 F Cl H NHCH(CH₃)COOCH₃ 6-215 Cl F H NHCH(CH₃)COOCH₃ 6-216 Cl Cl H NHCH(CH₃)COOCH₃ 6-217 H F H NHCH(CH₃)COOC₂H₅ 6-218 H Cl H NHCH(CH₃)COOC₂H₅ 6-219 F F H NHCH(CH₃)COOC₂H₅ 6-220 F Cl H NHCH(CH₃)COOC₂H₅ 6-221 Cl F H NHCH(CH₃)COOC₂H₅ 6-222 Cl Cl H NHCH(CH₃)COOC₂H₅ 6-223 H F H NHCH(CH₃)COOnC₃H₇ 6-224 H Cl H NHCH(CH₃)COOnC₃H₇ 6-225 F F H NHCH(CH₃)COOnC₃H₇

TABLE 72 X Y R¹ B 6-226 F Cl H NHCH(CH₃)COOnC₃H₇ 6-227 Cl F H NHCH(CH₃)COOnC₃H₇ 6-228 Cl Cl H NHCH(CH₃)COOnC₃H₇ 6-229 H F H NHCH(CH₃)COOnC₄H₉ 6-230 H Cl H NHCH(CH₃)COOnC₄H₉ 6-231 F F H NHCH(CH₃)COOnC₄H₉ 6-232 F Cl H NHCH(CH₃)COOnC₄H₉ 6-233 Cl F H NHCH(CH₃)COOnC₄H₉ 6-234 Cl Cl H NHCH(CH₃)COOnC₄H₉ 6-235 H F H NHCH(CH₃)COOnC₅H₁₁ 6-236 H Cl H NHCH(CH₃)COOnC₅H₁₁ 6-237 F F H NHCH(CH₃)COOnC₅H₁₁ 6-238 F Cl H NHCH(CH₃)COOnC₅H₁₁ 6-239 Cl F H NHCH(CH₃)COOnC₅H₁₁ 6-240 Cl Cl H NHCH(CH₃)COOnC₅H₁₁ 6-241 H F H NHCH(CH₃)COOiC₃H₇ 6-242 H Cl H NHCH(CH₃)COOiC₃H₇ 6-243 F F H NHCH(CH₃)COOiC₃H₇ 6-244 F Cl H NHCH(CH₃)COOiC₃H₇ 6-245 Cl F H NHCH(CH₃)COOiC₃H₇ 6-246 Cl Cl H NHCH(CH₃)COOiC₃H₇ 6-247 H F H NHCH(CH₃)COOcC₅H₉ 6-248 H Cl H NHCH(CH₃)COOcC₅H₉ 6-249 F F H NHCH(CH₃)COOcC₅H₉ 6-250 F Cl H NHCH(CH₃)COOcC₅H₉

TABLE 73 X Y R¹ B 6-251 Cl F H NHCH(CH₃)COOcC₅H₉ 6-252 Cl Cl H NHCH(CH₃)COOcC₅H₉ 6-253 H F H NHCH(CH₃)COOcC₆H₁₁ 6-254 H Cl H NHCH(CH₃)COOcC₆H₁₁ 6-255 F F H NHCH(CH₃)COOcC₆H₁₁ 6-256 F Cl H NHCH(CH₃)COOcC₆H₁₁ 6-257 Cl F H NHCH(CH₃)COOcC₆H₁₁ 6-258 Cl Cl H NHCH(CH₃)COOcC₆H₁₁ 6-259 H F H OCH₃ 6-260 H Cl H OCH₃ 6-261 F F H OCH₃ 6-262 F Cl H OCH₃ 6-263 Cl F H OCH₃ 6-264 Cl Cl H OCH₃ 6-265 H F H OC₂H₅ 6-266 H Cl H OC₂H₅ 6-267 F F H OC₂H₅ 6-268 F Cl H OC₂H₅ 6-269 Cl F H OC₂H₅ 6-270 Cl Cl H OC₂H₅ 6-271 H F H OiC₃H₇ 6-272 H Cl H OiC₃H₇ 6-273 F F H OiC₃H₇ 6-274 F Cl H OiC₃H₇ 6-275 Cl F H OiC₃H₇

TABLE 74 X Y R¹ B 6-276 Cl Cl H OiC₃H₇ 6-277 H F H OnC₃H₇ 6-278 H Cl H OnC₃H₇ 6-279 F F H OnC₃H₇ 6-280 F Cl H OnC₃H₇ 6-281 Cl F H OnC₃H₇ 6-282 Cl Cl H OnC₃H₇ 6-283 H F H OCH₂CH₂Cl 6-284 H Cl H OCH₂CH₂Cl 6-285 F F H OCH₂CH₂Cl 6-286 F Cl H OCH₂CH₂Cl 6-287 Cl F H OCH₂CH₂Cl 6-288 Cl Cl H OCH₂CH₂Cl 6-289 H F H OCF₂CF₂H 6-290 H Cl H OCF₂CF₂H 6-291 F F H OCF₂CF₂H 6-292 F Cl H OCF₂CF₂H 6-293 Cl F H OCF₂CF₂H 6-294 Cl Cl H OCF₂CF₂H 6-295 H F H OcC₅H₉ 6-296 H Cl H OcC₅H₉ 6-297 F F H OcC₅H₉ 6-298 F Cl H OcC₅H₉ 6-299 Cl F H OcC₅H₉ 6-300 Cl Cl H OcC₅H₉

TABLE 75 X Y R¹ B 6-301 H F H OcC₆H₁₁ 6-302 H Cl H OcC₆H₁₁ 6-303 F F H OcC₆H₁₁ 6-304 F Cl H OcC₆H₁₁ 6-305 Cl F H OcC₆H₁₁ 6-306 Cl Cl H OcC₆H₁₁ 6-307 H F H OCH₂CH═CH₂ 6-308 H Cl H OCH₂CH═CH₂ 6-309 F F H OCH₂CH═CH₂ 6-310 F Cl H OCH₂CH═CH₂ 6-311 Cl F H OCH₂CH═CH₂ 6-312 Cl Cl H OCH₂CH═CH₂ 6-313 H F H OCH₂CCl═CH₂ 6-314 H Cl H OCH₂CCl═CH₂ 6-315 F F H OCH₂CCl═CH₂ 6-316 F Cl H OCH₂CCl═CH₂ 6-317 Cl F H OCH₂CCl═CH₂ 6-318 Cl Cl H OCH₂CCl═CH₂ 6-319 H F H OCH₂CCl═CHCl 6-320 H Cl H OCH₂CCl═CHCl 6-321 F F H OCH₂CCl═CHCl 6-322 F Cl H OCH₂CCl═CHCl 6-323 Cl F H OCH₂CCl═CHCl 6-324 Cl Cl H OCH₂CCl═CHCl 6-325 H F H OCH(CH₃)CH═CH₂

TABLE 76 X Y R¹ B 6-326 H Cl H OCH(CH₃)CH═CH₂ 6-327 F F H OCH(CH₃)CH═CH₂ 6-328 F Cl H OCH(CH₃)CH═CH₂ 6-329 Cl F H OCH(CH₃)CH═CH₂ 6-330 Cl Cl H OCH(CH₃)CH═CH₂ 6-331 H F H OCH₂C(CH₃)═CH₂ 6-332 H Cl H OCH₂C(CH₃)═CH₂ 6-333 F F H OCH₂C(CH₃)═CH₂ 6-334 F Cl H OCH₂C(CH₃)═CH₂ 6-335 Cl F H OCH₂C(CH₃)═CH₂ 6-336 Cl Cl H OCH₂C(CH₃)═CH₂ 6-337 H F H OCH₂C≡CH 6-338 H Cl H OCH₂C≡CH 6-339 F F H OCH₂C≡CH 6-340 F Cl H OCH₂C≡CH 6-341 Cl F H OCH₂C≡CH 6-342 Cl Cl H OCH₂C≡CH 6-343 H F H OCH(CH₃)C≡CH 6-344 H Cl H OCH(CH₃)C≡CH 6-345 F F H OCH(CH₃)C≡CH 6-346 F Cl H OCH(CH₃)C≡CH 6-347 Cl F H OCH(CH₃)C≡CH 6-348 Cl Cl H OCH(CH₃)C≡CH 6-349 H F H OCH₂C≡CBr 6-350 H Cl H OCH₂C≡CBr

TABLE 77 X Y R¹ B 6-351 F F H OCH₂C≡CBr 6-352 F Cl H OCH₂C≡CBr 6-353 Cl F H OCH₂C≡CBr 6-354 Cl Cl H OCH₂C≡CBr 6-355 H F H OCH₂C≡CCl 6-356 H Cl H OCH₂C≡CCl 6-357 F F H OCH₂C≡CCl 6-358 F Cl H OCH₂C≡CCl 6-359 Cl F H OCH₂C≡CCl 6-360 Cl Cl H OCH₂C≡CCl 6-361 H F H OCH₂C≡CCH₂Cl 6-362 H Cl H OCH₂C≡CCH₂Cl 6-363 F F H OCH₂C≡CCH₂Cl 6-364 F Cl H OCH₂C≡CCH₂Cl 6-365 Cl F H OCH₂C≡CCH₂Cl 6-366 Cl Cl H OCH₂C≡CCH₂Cl 6-367 H F H OCH₂CN 6-368 H Cl H OCH₂CN 6-369 F F H OCH₂CN 6-370 F Cl H OCH₂CN 6-371 Cl F H OCH₂CN 6-372 Cl Cl H OCH₂CN 6-373 H F H OCH₂OCH₃ 6-374 H Cl H OCH₂OCH₃ 6-375 F F H OCH₂OCH₃

TABLE 78 X Y R¹ B 6-376 F Cl H OCH₂OCH₃ 6-377 Cl F H OCH₂OCH₃ 6-378 Cl Cl H OCH₂OCH₃ 6-379 H F H OCH₂OC₂H₅ 6-380 H Cl H OCH₂OC₂H₅ 6-381 F F H OCH₂OC₂H₅ 6-382 F Cl H OCH₂OC₂H₅ 6-383 Cl F H OCH₂OC₂H₅ 6-384 Cl Cl H OCH₂OC₂H₅ 6-385 H F H OCH₂SCH₃ 6-386 H Cl H OCH₂SCH₃ 6-387 F F H OCH₂SCH₃ 6-388 F Cl H OCH₂SCH₃ 6-389 Cl F H OCH₂SCH₃ 6-390 Cl Cl H OCH₂SCH₃ 6-391 H F H OCH₂COOH 6-392 H Cl H OCH₂COOH 6-393 F F H OCH₂COOH 6-394 F Cl H OCH₂COOH 6-395 Cl F H OCH₂COOH 6-396 Cl Cl H OCH₂COOH 6-397 H F H OCH₂COOCH₃ 6-398 H Cl H OCH₂COOCH₃ 6-399 F F H OCH₂COOCH₃ 6-400 F Cl H OCH₂COOCH₃

TABLE 79 X Y R¹ B 6-401 Cl F H OCH₂COOCH₃ 6-402 Cl Cl H OCH₂COOCH₃ 6-403 H F H OCH₂COOC₂H₅ 6-404 H Cl H OCH₂COOC₂H₅ 6-405 F F H OCH₂COOC₂H₅ 6-406 F Cl H OCH₂COOC₂H₅ 6-407 Cl F H OCH₂COOC₂H₅ 6-408 Cl Cl H OCH₂COOC₂H₅ 6-409 H F H OCH₂COOnC₃H₇ 6-410 H Cl H OCH₂COOnC₃H₇ 6-411 F F H OCH₂COOnC₃H₇ 6-412 F Cl H OCH₂COOnC₃H₇ 6-413 Cl F H OCH₂COOnC₃H₇ 6-414 Cl Cl H OCH₂COOnC₃H₇ 6-415 H F H OCH₂COOnC₄H₉ 6-416 H Cl H OCH₂COOnC₄H₉ 6-417 F F H OCH₂COOnC₄H₉ 6-418 F Cl H OCH₂COOnC₄H₉ 6-419 Cl F H OCH₂COOnC₄H₉ 6-420 Cl Cl H OCH₂COOnC₄H₉ 6-421 H F H OCH₂COOnC₅H₁₁ 6-422 H Cl H OCH₂COOnC₅H₁₁ 6-423 F F H OCH₂COOnC₅H₁₁ 6-424 F Cl H OCH₂COOnC₅H₁₁ 6-425 Cl F H OCH₂COOnC₅H₁₁

TABLE 80 X Y R¹ B 6-426 Cl Cl H OCH₂COOnC₅H₁₁ 6-427 H F H OCH₂COOiC₃H₇ 6-428 H Cl H OCH₂COOiC₃H₇ 6-429 F F H OCH₂COOiC₃H₇ 6-430 F Cl H OCH₂COOiC₃H₇ 6-431 Cl F H OCH₂COOiC₃H₇ 6-432 Cl Cl H OCH₂COOiC₃H₇ 6-433 H F H OCH₂COOcC₅H₉ 6-434 H Cl H OCH₂COOcC₅H₉ 6-435 F F H OCH₂COOcC₅H₉ 6-436 F Cl H OCH₂COOcC₅H₉ 6-437 Cl F H OCH₂COOcC₅H₉ 6-438 Cl Cl H OCH₂COOcC₅H₉ 6-439 H F H OCH₂COOcC₆H₁₁ 6-440 H Cl H OCH₂COOcC₆H₁₁ 6-441 F F H OCH₂COOcC₆H₁₁ 6-442 F Cl H OCH₂COOcC₆H₁₁ 6-443 Cl F H OCH₂COOcC₆H₁₁ 6-444 Cl Cl H OCH₂COOcC₆H₁₁ 6-445 H F H OCH(CH₃)COOH 6-446 H Cl H OCH(CH₃)COOH 6-447 F F H OCH(CH₃)COOH 6-448 F Cl H OCH(CH₃)COOH 6-449 Cl F H OCH(CH₃)COOH 6-450 Cl Cl H OCH(CH₃)COOH

TABLE 81 X Y R¹ B 6-451 H F H OCH(CH₃)COOCH₃ 6-452 H Cl H OCH(CH₃)COOCH₃ 6-453 F F H OCH(CH₃)COOCH₃ 6-454 F Cl H OCH(CH₃)COOCH₃ 6-455 Cl F H OCH(CH₃)COOCH₃ 6-456 Cl Cl H OCH(CH₃)COOCH₃ 6-457 H F H OCH(CH₃)COOC₂H₅ 6-458 H Cl H OCH(CH₃)COOC₂H₅ 6-459 F F H OCH(CH₃)COOC₂H₅ 6-460 F Cl H OCH(CH₃)COOC₂H₅ 6-461 Cl F H OCH(CH₃)COOC₂H₅ 6-462 Cl Cl H OCH(CH₃)COOC₂H₅ 6-463 H F H OCH(CH₃)COOnC₃H₇ 6-464 H Cl H OCH(CH₃)COOnC₃H₇ 6-465 F F H OCH(CH₃)COOnC₃H₇ 6-466 F Cl H OCH(CH₃)COOnC₃H₇ 6-467 Cl F H OCH(CH₃)COOnC₃H₇ 6-468 Cl Cl H OCH(CH₃)COOnC₃H₇ 6-469 H F H OCH(CH₃)COOnC₄H₉ 6-470 H Cl H OCH(CH₃)COOnC₄H₉ 6-471 F F H OCH(CH₃)COOnC₄H₉ 6-472 F Cl H OCH(CH₃)COOnC₄H₉ 6-473 Cl F H OCH(CH₃)COOnC₄H₉ 6-474 Cl Cl H OCH(CH₃)COOnC₄H₉ 6-475 H F H OCH(CH₃)COOnC₅H₁₁

TABLE 82 X Y R¹ B 6-476 H Cl H OCH(CH₃)COOnC₅H₁₁ 6-477 F F H OCH(CH₃)COOnC₅H₁₁ 6-478 F Cl H OCH(CH₃)COOnC₅H₁₁ 6-479 Cl F H OCH(CH₃)COOnC₅H₁₁ 6-480 Cl Cl H OCH(CH₃)COOnC₅H₁₁ 6-481 H F H OCH(CH₃)COOiC₃H₇ 6-482 H Cl H OCH(CH₃)COOiC₃H₇ 6-483 F F H OCH(CH₃)COOiC₃H₇ 6-484 F Cl H OCH(CH₃)COOiC₃H₇ 6-485 Cl F H OCH(CH₃)COOiC₃H₇ 6-486 Cl Cl H OCH(CH₃)COOiC₃H₇ 6-487 H F H OCH(CH₃)COOcC₅H₉ 6-488 H Cl H OCH(CH₃)COOcC₅H₉ 6-489 F F H OCH(CH₃)COOcC₅H₉ 6-490 F Cl H OCH(CH₃)COOcC₅H₉ 6-491 Cl F H OCH(CH₃)COOcC₅H₉ 6-492 Cl Cl H OCH(CH₃)COOcC₅H₉ 6-493 H F H OCH(CH₃)COOcC₆H₁₁ 6-494 H Cl H OCH(CH₃)COOcC₆H₁₁ 6-495 F F H OCH(CH₃)COOcC₆H₁₁ 6-496 F Cl H OCH(CH₃)COOcC₆H₁₁ 6-497 Cl F H OCH(CH₃)COOcC₆H₁₁ 6-498 Cl Cl H OCH(CH₃)COOcC₆H₁₁ 6-499 H F H OCH₂CONH₂ 6-500 H Cl H OCH₂CONH₂

TABLE 83 X Y R¹ B 6-501 F F H OCH₂CONH₂ 6-502 F Cl H OCH₂CONH₂ 6-503 Cl F H OCH₂CONH₂ 6-504 Cl Cl H OCH₂CONH₂ 6-505 H F H OCH₂CONHCH₃ 6-506 H Cl H OCH₂CONHCH₃ 6-507 F F H OCH₂CONHCH₃ 6-508 F Cl H OCH₂CONHCH₃ 6-509 Cl F H OCH₂CONHCH₃ 6-510 Cl Cl H OCH₂CONHCH₃ 6-511 H F H OCH₂CON(CH₃)₂ 6-512 H Cl H OCH₂CON(CH₃)₂ 6-513 F F H OCH₂CON(CH₃)₂ 6-514 F Cl H OCH₂CON(CH₃)₂ 6-515 Cl F H OCH₂CON(CH₃)₂ 6-516 Cl Cl H OCH₂CON(CH₃)₂ 6-517 H F H OCH₂CON(C₂H₅)₂ 6-518 H Cl H OCH₂CON(C₂H₅)₂ 6-519 F F H OCH₂CON(C₂H₅)₂ 6-520 F Cl H OCH₂CON(C₂H₅)₂ 6-521 Cl F H OCH₂CON(C₂H₅)₂ 6-522 Cl Cl H OCH₂CON(C₂H₅)₂ 6-523 H F H OCH₂CON(CH₃)C₂H₅ 6-524 H Cl H OCH₂CON(CH₃)C₂H₅ 6-525 F F H OCH₂CON(CH₃)C₂H₅

TABLE 84 X Y R¹ B 6-526 F Cl H OCH₂CON(CH₃)C₂H₅ 6-527 Cl F H OCH₂CON(CH₃)C₂H₅ 6-528 Cl Cl H OCH₂CON(CH₃)C₂H₅ 6-529 H F H OCH₂CON(tetramethylene) 6-530 H Cl H OCH₂CON(tetramethylene) 6-531 F F H OCH₂CON(tetramethylene) 6-532 F Cl H OCH₂CON(tetramethylene) 6-533 Cl F H OCH₂CON(tetramethylene) 6-534 Cl Cl H OCH₂CON(tetramethylene) 6-535 H F H OCH₂CON(pentamethylene) 6-536 H Cl H OCH₂CON(pentamethylene) 6-537 F F H OCH₂CON(pentamethylene) 6-538 F Cl H OCH₂CON(pentamethylene) 6-539 Cl F H OCH₂CON(pentamethylene) 6-540 Cl Cl H OCH₂CON(pentamethylene) 6-541 H F H OCH₂CON(ethyleneoxyethylene) 6-542 H Cl H OCH₂CON(ethyleneoxyethylene) 6-543 F F H OCH₂CON(ethyleneoxyethylene) 6-544 F Cl H OCH₂CON(ethyleneoxyethylene) 6-545 Cl F H OCH₂CON(ethyleneoxyethylene) 6-546 Cl Cl H OCH₂CON(ethyleneoxyethylene) 6-547 H F H OCH(CH₃)CONH₂ 6-548 H Cl H OCH(CH₃)CONH₂ 6-549 F F H OCH(CH₃)CONH₂ 6-550 F Cl H OCH(CH₃)CONH₂

TABLE 85 X Y R¹ B 6-551 Cl F H OCH(CH₃)CONH₂ 6-552 Cl Cl H OCH(CH₃)CONH₂ 6-553 H F H OCH(CH₃)CONHCH₃ 6-554 H Cl H OCH(CH₃)CONHCH₃ 6-555 F F H OCH(CH₃)CONHCH₃ 6-556 F Cl H OCH(CH₃)CONHCH₃ 6-557 Cl F H OCH(CH₃)CONHCH₃ 6-558 Cl Cl H OCH(CH₃)CONHCH₃ 6-559 H F H OCH(CH₃)CON(CH₃)₂ 6-560 H Cl H OCH(CH₃)CON(CH₃)₂ 6-561 F F H OCH(CH₃)CON(CH₃)₂ 6-562 F Cl H OCH(CH₃)CON(CH₃)₂ 6-563 Cl F H OCH(CH₃)CON(CH₃)₂ 6-564 Cl Cl H OCH(CH₃)CON(CH₃)₂ 6-565 H F H OCH(CH₃)CON(C₂H₅)₂ 6-566 H Cl H OCH(CH₃)CON(C₂H₅)₂ 6-567 F F H OCH(CH₃)CON(C₂H₅)₂ 6-568 F Cl H OCH(CH₃)CON(C₂H₅)₂ 6-569 Cl F H OCH(CH₃)CON(C₂H₅)₂ 6-570 Cl Cl H OCH(CH₃)CON(C₂H₅)₂ 6-571 H F H OCH(CH₃)CON(CH₃)C₂H₅ 6-572 H Cl H OCH(CH₃)CON(CH₃)C₂H₅ 6-573 F F H OCH(CH₃)CON(CH₃)C₂H₅ 6-574 F Cl H OCH(CH₃)CON(CH₃)C₂H₅ 6-575 Cl F H OCH(CH₃)CON(CH₃)C₂H₅

TABLE 86 X Y R¹ B 6-576 Cl Cl H OCH(CH₃)CON(CH₃)C₂H₅ 6-577 H F H OCH(CH₃)CON(tetramethylene) 6-578 H Cl H OCH(CH₃)CON(tetramethylene) 6-579 F F H OCH(CH₃)CON(tetramethylene) 6-580 F Cl H OCH(CH₃)CON(tetramethylene) 6-581 Cl F H OCH(CH₃)CON(tetramethylene) 6-582 Cl Cl H OCH(CH₃)CON(tetramethylene) 6-583 H F H OCH(CH₃)CON(pentamethylene) 6-584 H Cl H OCH(CH₃)CON(pentamethylene) 6-585 F F H OCH(CH₃)CON(pentamethylene) 6-586 F Cl H OCH(CH₃)CON(pentamethylene) 6-587 Cl F H OCH(CH₃)CON(pentamethylene) 6-588 Cl Cl H OCH(CH₃)CON(pentamethylene) 6-589 H F H OCH(CH₃)CON(ethyleneoxyethylene) 6-590 H Cl H OCH(CH₃)CON(ethyleneoxyethylene) 6-591 F F H OCH(CH₃)CON(ethyleneoxyethylene) 6-592 F Cl H OCH(CH₃)CON(ethyleneoxyethylene) 6-593 Cl F H OCH(CH₃)CON(ethyleneoxyethylene) 6-594 Cl Cl H OCH(CH₃)CON(ethyleneoxyethylene) 6-595 H F H OCH₂COON(CH₃)₂ 6-596 H Cl H OCH₂COON(CH₃)₂ 6-597 F F H OCH₂COON(CH₃)₂ 6-598 F Cl H OCH₂COON(CH₃)₂ 6-599 Cl F H OCH₂COON(CH₃)₂ 6-600 Cl Cl H OCH₂COON(CH₃)₂

TABLE 87 X Y R¹ B 6-601 H F H OCH₂COON(C₂H₅)₂ 6-602 H Cl H OCH₂COON(C₂H₅)₂ 6-603 F F H OCH₂COON(C₂H₅)₂ 6-604 F Cl H OCH₂COON(C₂H₅)₂ 6-605 Cl F H OCH₂COON(C₂H₅)₂ 6-606 Cl Cl H OCH₂COON(C₂H₅)₂ 6-607 H F H OCH(CH₃)COON(CH₃)₂ 6-608 H Cl H OCH(CH₃)COON(CH₃)₂ 6-609 F F H OCH(CH₃)COON(CH₃)₂ 6-610 F Cl H OCH(CH₃)COON(CH₃)₂ 6-611 Cl F H OCH(CH₃)COON(CH₃)₂ 6-612 Cl Cl H OCH(CH₃)COON(CH₃)₂ 6-613 H F H OCH(CH₃)COON(C₂H₅)₂ 6-614 H Cl H OCH(CH₃)COON(C₂H₅)₂ 6-615 F F H OCH(CH₃)COON(C₂H₅)₂ 6-616 F Cl H OCH(CH₃)COON(C₂H₅)₂ 6-617 Cl F H OCH(CH₃)COON(C₂H₅)₂ 6-618 Cl Cl H OCH(CH₃)COON(C₂H₅)₂ 6-619 H F H SCH₃ 6-620 H Cl H SCH₃ 6-621 F F H SCH₃ 6-622 F Cl H SCH₃ 6-623 Cl F H SCH₃ 6-624 Cl Cl H SCH₃ 6-625 H F H SC₂H₅

TABLE 88 X Y R¹ B 6-626 H Cl H SC₂H₅ 6-627 F F H SC₂H₅ 6-628 F Cl H SC₂H₅ 6-629 Cl F H SC₂H₅ 6-630 Cl Cl H SC₂H₅ 6-631 H F H SiC₃H₇ 6-632 H Cl H SiC₃H₇ 6-633 F F H SiC₃H₇ 6-634 F Cl H SiC₃H₇ 6-635 Cl F H SiC₃H₇ 6-636 Cl Cl H SiC₃H₇ 6-637 H F H SnC₃H₇ 6-638 H Cl H SnC₃H₇ 6-639 F F H SnC₃H₇ 6-640 F Cl H SnC₃H₇ 6-641 Cl F H SnC₃H₇ 6-642 Cl Cl H SnC₃H₇ 6-643 H F H SCH₂CH₂Cl 6-644 H Cl H SCH₂CH₂Cl 6-645 F F H SCH₂CH₂Cl 6-646 F Cl H SCH₂CH₂Cl 6-647 Cl F H SCH₂CH₂Cl 6-648 Cl Cl H SCH₂CH₂Cl 6-649 H F H ScC₅H₉ 6-650 H Cl H ScC₅H₉

TABLE 89 X Y R¹ B 6-651 F F H ScC₅H₉ 6-652 F Cl H ScC₅H₉ 6-653 Cl F H ScC₅H₉ 6-654 Cl Cl H ScC₅H₉ 6-655 H F H ScC₆H₁₁ 6-656 H Cl H ScC₆H₁₁ 6-657 F F H ScC₆H₁₁ 6-658 F Cl H ScC₆H₁₁ 6-659 Cl F H ScC₆H₁₁ 6-660 Cl Cl H ScC₆H₁₁ 6-661 H F H SCH₂CH═CH₂ 6-662 H Cl H SCH₂CH═CH₂ 6-663 F F H SCH₂CH═CH₂ 6-664 F Cl H SCH₂CH═CH₂ 6-665 Cl F H SCH₂CH═CH₂ 6-666 Cl Cl H SCH₂CH═CH₂ 6-667 H F H SCH₂CCl═CH₂ 6-668 H Cl H SCH₂CCl═CH₂ 6-669 F F H SCH₂CCl═CH₂ 6-670 F Cl H SCH₂CCl═CH₂ 6-671 Cl F H SCH₂CCl═CH₂ 6-672 Cl Cl H SCH₂CCl═CH₂ 6-673 H F H SCH₂CCl═CHCl 6-674 H Cl H SCH₂CCl═CHCl 6-675 F F H SCH₂CCl═CHCl

TABLE 90 X Y R¹ B 6-676 F Cl H SCH₂CCl═CHCl 6-677 Cl F H SCH₂CCl═CHCl 6-678 Cl Cl H SCH₂CCl═CHCl 6-679 H F H SCH(CH₃)CH═CH₂ 6-680 H Cl H SCH(CH₃)CH═CH₂ 6-681 F F H SCH(CH₃)CH═CH₂ 6-682 F Cl H SCH(CH₃)CH═CH₂ 6-683 Cl F H SCH(CH₃)CH═CH₂ 6-684 Cl Cl H SCH(CH₃)CH═CH₂ 6-685 H F H SCH₂C≡CH 6-686 H Cl H SCH₂C≡CH 6-687 F F H SCH₂C≡CH 6-688 F Cl H SCH₂C≡CH 6-689 Cl F H SCH₂C≡CH 6-690 Cl Cl H SCH₂C≡CH 6-691 H F H SCH(CH₃)C≡CH 6-692 H Cl H SCH(CH₃)C≡CH 6-693 F F H SCH(CH₃)C≡CH 6-694 F Cl H SCH(CH₃)C≡CH 6-695 Cl F H SCH(CH₃)C≡CH 6-696 Cl Cl H SCH(CH₃)C≡CH 6-697 H F H SCH₂COOH 6-698 H Cl H SCH₂COOH 6-699 F F H SCH₂COOH 6-700 F Cl H SCH₂COOH

TABLE 91 X Y R¹ B 6-701 Cl F H SCH₂COOH 6-702 Cl Cl H SCH₂COOH 6-703 H F H SCH₂COOCH₃ 6-704 H Cl H SCH₂COOCH₃ 6-705 F F H SCH₂COOCH₃ 6-706 F Cl H SCH₂COOCH₃ 6-707 Cl F H SCH₂COOCH₃ 6-708 Cl Cl H SCH₂COOCH₃ 6-709 H F H SCH₂COOC₂H₅ 6-710 H Cl H SCH₂COOC₂H₅ 6-711 F F H SCH₂COOC₂H₅ 6-712 F Cl H SCH₂COOC₂H₅ 6-713 Cl F H SCH₂COOC₂H₅ 6-714 Cl Cl H SCH₂COOC₂H₅ 6-715 H F H SCH₂COOnC₃H₇ 6-716 H Cl H SCH₂COOnC₃H₇ 6-717 F F H SCH₂COOnC₃H₇ 6-718 F Cl H SCH₂COOnC₃H₇ 6-719 Cl F H SCH₂COOnC₃H₇ 6-720 Cl Cl H SCH₂COOnC₃H₇ 6-721 H F H SCH₂COOnC₄H₉ 6-722 H Cl H SCH₂COOnC₄H₉ 6-723 F F H SCH₂COOnC₄H₉ 6-724 F Cl H SCH₂COOnC₄H₉ 6-725 Cl F H SCH₂COOnC₄H₉

TABLE 92 X Y R¹ B 6-726 Cl Cl H SCH₂COOnC₄H₉ 6-727 H F H SCH₂COOnC₅H₁₁ 6-728 H Cl H SCH₂COOnC₅H₁₁ 6-729 F F H SCH₂COOnC₅H₁₁ 6-730 F Cl H SCH₂COOnC₅H₁₁ 6-731 Cl F H SCH₂COOnC₅H₁₁ 6-732 Cl Cl H SCH₂COOnC₅H₁₁ 6-733 H F H SCH₂COOiC₃H₇ 6-734 H Cl H SCH₂COOiC₃H₇ 6-735 F F H SCH₂COOiC₃H₇ 6-736 F Cl H SCH₂COOiC₃H₇ 6-737 Cl F H SCH₂COOiC₃H₇ 6-738 Cl Cl H SCH₂COOiC₃H₇ 6-739 H F H SCH₂COOcC₅H₉ 6-740 H Cl H SCH₂COOcC₅H₉ 6-741 F F H SCH₂COOcC₅H₉ 6-742 F Cl H SCH₂COOcC₅H₉ 6-743 Cl F H SCH₂COOcC₅H₉ 6-744 Cl Cl H SCH₂COOcC₅H₉ 6-745 H F H SCH₂COOcC₆H₁₁ 6-746 H Cl H SCH₂COOcC₆H₁₁ 6-747 F F H SCH₂COOcC₆H₁₁ 6-748 F Cl H SCH₂COOcC₆H₁₁ 6-749 Cl F H SCH₂COOcC₆H₁₁ 6-750 Cl Cl H SCH₂COOcC₆H₁₁

TABLE 93 X Y R¹ B 6-751 H F H SCH(CH₃)COOH 6-752 H Cl H SCH(CH₃)COOH 6-753 F F H SCH(CH₃)COOH 6-754 F Cl H SCH(CH₃)COOH 6-755 Cl F H SCH(CH₃)COOH 6-756 Cl Cl H SCH(CH₃)COOH 6-757 H F H SCH(CH₃)COOCH₃ 6-758 H Cl H SCH(CH₃)COOCH₃ 6-759 F F H SCH(CH₃)COOCH₃ 6-760 F Cl H SCH(CH₃)COOCH₃ 6-761 Cl F H SCH(CH₃)COOCH₃ 6-762 Cl Cl H SCH(CH₃)COOCH₃ 6-763 H F H SCH(CH₃)COOC₂H₅ 6-764 H Cl H SCH(CH₃)COOC₂H₅ 6-765 F F H SCH(CH₃)COOC₂H₅ 6-766 F Cl H SCH(CH₃)COOC₂H₅ 6-767 Cl F H SCH(CH₃)COOC₂H₅ 6-768 Cl Cl H SCH(CH₃)COOC₂H₅ 6-769 H F H SCH(CH₃)COOnC₃H₇ 6-770 H Cl H SCH(CH₃)COOnC₃H₇ 6-771 F F H SCH(CH₃)COOnC₃H₇ 6-772 F Cl H SCH(CH₃)COOnC₃H₇ 6-773 Cl F H SCH(CH₃)COOnC₃H₇ 6-774 Cl Cl H SCH(CH₃)COOnC₃H₇ 6-775 H F H SCH(CH₃)COOnC₄H₉

TABLE 94 X Y R¹ B 6-776 H Cl H SCH(CH₃)COOnC₄H₉ 6-777 F F H SCH(CH₃)COOnC₄H₉ 6-778 F Cl H SCH(CH₃)COOnC₄H₉ 6-779 Cl F H SCH(CH₃)COOnC₄H₉ 6-780 Cl Cl H SCH(CH₃)COOnC₄H₉ 6-781 H F H SCH(CH₃)COOnC₅H₁₁ 6-782 H Cl H SCH(CH₃)COOnC₅H₁₁ 6-783 F F H SCH(CH₃)COOnC₅H₁₁ 6-784 F Cl H SCH(CH₃)COOnC₅H₁₁ 6-785 Cl F H SCH(CH₃)COOnC₅H₁₁ 6-786 Cl Cl H SCH(CH₃)COOnC₅H₁₁ 6-787 H F H SCH(CH₃)COOiC₃H₇ 6-788 H Cl H SCH(CH₃)COOiC₃H₇ 6-789 F F H SCH(CH₃)COOiC₃H₇ 6-790 F Cl H SCH(CH₃)COOiC₃H₇ 6-791 Cl F H SCH(CH₃)COOiC₃H₇ 6-792 Cl Cl H SCH(CH₃)COOiC₃H₇ 6-793 H F H SCH(CH₃)COOcC₅H₉ 6-794 H Cl H SCH(CH₃)COOcC₅H₉ 6-795 F F H SCH(CH₃)COOcC₅H₉ 6-796 F Cl H SCH(CH₃)COOcC₅H₉ 6-797 Cl F H SCH(CH₃)COOcC₅H₉ 6-798 Cl Cl H SCH(CH₃)COOcC₅H₉ 6-799 H F H SCH(CH₃)COOcC₆H₁₁ 6-800 H Cl H SCH(CH₃)COOcC₆H₁₁

TABLE 95 X Y R¹ B 6-801 F F H SCH(CH₃)COOcC₆H₁₁ 6-802 F Cl H SCH(CH₃)COOcC₆H₁₁ 6-803 Cl F H SCH(CH₃)COOcC₆H₁₁ 6-804 Cl Cl H SCH(CH₃)COOcC₆H₁₁ 6-805 H F H SCH₂CONH₂ 6-806 H Cl H SCH₂CONH₂ 6-807 F F H SCH₂CONH₂ 6-808 F Cl H SCH₂CONH₂ 6-809 Cl F H SCH₂CONH₂ 6-810 Cl Cl H SCH₂CONH₂ 6-811 H F H SCH₂CONHCH₃ 6-812 H Cl H SCH₂CONHCH₃ 6-813 F F H SCH₂CONHCH₃ 6-814 F Cl H SCH₂CONHCH₃ 6-815 Cl F H SCH₂CONHCH₃ 6-816 Cl Cl H SCH₂CONHCH₃ 6-817 H F H SCH₂CON(CH₃)₂ 6-818 H Cl H SCH₂CON(CH₃)₂ 6-819 F F H SCH₂CON(CH₃)₂ 6-820 F Cl H SCH₂CON(CH₃)₂ 6-821 Cl F H SCH₂CON(CH₃)₂ 6-822 Cl Cl H SCH₂CON(CH₃)₂ 6-823 H F H SCH₂CON(C₂H₅)₂ 6-824 H Cl H SCH₂CON(C₂H₅)₂ 6-825 F F H SCH₂CON(C₂H₅)₂

TABLE 96 X Y R¹ B 6-826 F Cl H SCH₂CON(C₂H₅)₂ 6-827 Cl F H SCH₂CON(C₂H₅)₂ 6-828 Cl Cl H SCH₂CON(C₂H₅)₂ 6-829 H F H SCH₂CON(CH₃)C₂H₅ 6-830 H Cl H SCH₂CON(CH₃)C₂H₅ 6-831 F F H SCH₂CON(CH₃)C₂H₅ 6-832 F Cl H SCH₂CON(CH₃)C₂H₅ 6-833 Cl F H SCH₂CON(CH₃)C₂H₅ 6-834 Cl Cl H SCH₂CON(CH₃)C₂H₅ 6-835 H F H SCH₂CON(tetramethylene) 6-836 H Cl H SCH₂CON(tetramethylene) 6-837 F F H SCH₂CON(tetramethylene) 6-838 F Cl H SCH₂CON(tetramethylene) 6-839 Cl F H SCH₂CON(tetramethylene) 6-840 Cl Cl H SCH₂CON(tetramethylene) 6-841 H F H SCH₂CON(pentamethylene) 6-842 H Cl H SCH₂CON(pentamethylene) 6-843 F F H SCH₂CON(pentamethylene) 6-844 F Cl H SCH₂CON(pentamethylene) 6-845 Cl F H SCH₂CON(pentamethylene) 6-846 Cl Cl H SCH₂CON(pentamethylene) 6-847 H F H SCH₂CON(ethyleneoxyethylene) 6-848 H Cl H SCH₂CON(ethyleneoxyethylene) 6-849 F F H SCH₂CON(ethyleneoxyethylene) 6-850 F Cl H SCH₂CON(ethyleneoxyethylene)

TABLE 97 X Y R¹ B 6-851 Cl F H SCH₂CON(ethyleneoxyethylene) 6-852 Cl Cl H SCH₂CON(ethyleneoxyethylene) 6-853 H F H SCH(CH₃)CONH₂ 6-854 H Cl H SCH(CH₃)CONH₂ 6-855 F F H SCH(CH₃)CONH₂ 6-856 F Cl H SCH(CH₃)CONH₂ 6-857 Cl F H SCH(CH₃)CONH₂ 6-858 Cl Cl H SCH(CH₃)CONH₂ 6-859 H F H SCH(CH₃)CONHCH₃ 6-860 H Cl H SCH(CH₃)CONHCH₃ 6-861 F F H SCH(CH₃)CONHCH₃ 6-862 F Cl H SCH(CH₃)CONHCH₃ 6-863 Cl F H SCH(CH₃)CONHCH₃ 6-864 Cl Cl H SCH(CH₃)CONHCH₃ 6-865 H F H SCH(CH₃)CON(CH₃)₂ 6-866 H Cl H SCH(CH₃)CON(CH₃)₂ 6-867 F F H SCH(CH₃)CON(CH₃)₂ 6-868 F Cl H SCH(CH₃)CON(CH₃)₂ 6-869 Cl F H SCH(CH₃)CON(CH₃)₂ 6-870 Cl Cl H SCH(CH₃)CON(CH₃)₂ 6-871 H F H SCH(CH₃)CON(C₂H₅)₂ 6-872 H Cl H SCH(CH₃)CON(C₂H₅)₂ 6-873 F F H SCH(CH₃)CON(C₂H₅)₂ 6-874 F Cl H SCH(CH₃)CON(C₂H₅)₂ 6-875 Cl F H SCH(CH₃)CON(C₂H₅)₂

TABLE 98 X Y R¹ B 6-876 Cl Cl H SCH(CH₃)CON(C₂H₅)₂ 6-877 H F H SCH(CH₃)CON(CH₃)C₂H₅ 6-878 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 6-879 F F H SCH(CH₃)CON(CH₃)C₂H₅ 6-880 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 6-881 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 6-882 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 6-883 H F H SCH(CH₃)CON(CH₃)C₂H₅ 6-884 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 6-885 F F H SCH(CH₃)CON(CH₃)C₂H₅ 6-886 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 6-887 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 6-888 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 6-889 H F H SCH(CH₃)CON(tetramethylene) 6-890 H Cl H SCH(CH₃)CON(tetramethylene) 6-891 F F H SCH(CH₃)CON(tetramethylene) 6-892 F Cl H SCH(CH₃)CON(tetramethylene) 6-893 Cl F H SCH(CH₃)CON(tetramethylene) 6-894 Cl Cl H SCH(CH₃)CON(tetramethylene) 6-895 H F H SCH(CH₃)CON(pentamethylene) 6-896 H Cl H SCH(CH₃)CON(pentamethylene) 6-897 F F H SCH(CH₃)CON(pentamethylene) 6-898 F Cl H SCH(CH₃)CON(pentamethylene) 6-899 Cl F H SCH(CH₃)CON(pentamethylene) 6-900 Cl Cl H SCH(CH₃)CON(pentamethylene)

TABLE 99 X Y R¹ B 6-901 H F H SCH(CH₃)CON(ethyleneoxyethylene) 6-902 H Cl H SCH(CH₃)CON(ethyleneoxyethylene) 6-903 F F H SCH(CH₃)CON(ethyleneoxyethylene) 6-904 F Cl H SCH(CH₃)CON(ethyleneoxyethylene) 6-905 Cl F H SCH(CH₃)CON(ethyleneoxyethylene) 6-906 Cl Cl H SCH(CH₃)CON(ethyleneoxyethylene) 6-907 H F H SO₂OCH₃ 6-908 H Cl H SO₂OCH₃ 6-909 F F H SO₂OCH₃ 6-910 F Cl H SO₂OCH₃ 6-911 Cl F H SO₂OCH₃ 6-912 Cl Cl H SO₂OCH₃ 6-913 H F H SO₂OC₂H₅ 6-914 H Cl H SO₂OC₂H₅ 6-915 F F H SO₂OC₂H₅ 6-916 F Cl H SO₂OC₂H₅ 6-917 Cl F H SO₂OC₂H₅ 6-918 Cl Cl H SO₂OC₂H₅ 6-919 H F H SO₂OiC₃H₇ 6-920 H Cl H SO₂OiC₃H₇ 6-921 F F H SO₂OiC₃H₇ 6-922 F Cl H SO₂OiC₃H₇ 6-923 Cl F H SO₂OiC₃H₇ 6-924 Cl Cl H SO₂OiC₃H₇ 6-925 H F H SO₂OCH₂CH═CH₂

TABLE 100 X Y R¹ B 6-926 H Cl H SO₂OCH₂CH═CH₂ 6-927 F F H SO₂OCH₂CH═CH₂ 6-928 F Cl H SO₂OCH₂CH═CH₂ 6-929 Cl F H SO₂OCH₂CH═CH₂ 6-930 Cl Cl H SO₂OCH₂CH═CH₂ 6-931 H F H SO₂N(CH₃)₂ 6-932 H Cl H SO₂N(CH₃)₂ 6-933 F F H SO₂N(CH₃)₂ 6-934 F Cl H SO₂N(CH₃)₂ 6-935 Cl F H SO₂N(CH₃)₂ 6-936 Cl Cl H SO₂N(CH₃)₂ 6-937 H F H SO₂N(C₂H₅)₂ 6-938 H Cl H SO₂N(C₂H₅)₂ 6-939 F F H SO₂N(C₂H₅)₂ 6-940 F Cl H SO₂N(C₂H₅)₂ 6-941 Cl F H SO₂N(C₂H₅)₂ 6-942 Cl Cl H SO₂N(C₂H₅)₂ 6-943 H F H COOH 6-944 H Cl H COOH 6-945 F F H COOH 6-946 F Cl H COOH 6-947 Cl F H COOH 6-948 Cl Cl H COOH 6-949 H F H COOCH₃ 6-950 H Cl H COOCH₃

TABLE 101 X Y R¹ B 6-951 F F H COOCH₃ 6-952 F Cl H COOCH₃ 6-953 Cl F H COOCH₃ 6-954 Cl Cl H COOCH₃ 6-955 H F H COOC₂H₅ 6-956 H Cl H COOC₂H₅ 6-957 F F H COOC₂H₅ 6-958 F Cl H COOC₂H₅ 6-959 Cl F H COOC₂H₅ 6-960 Cl Cl H COOC₂H₅ 6-961 H F H COOnC₃H₇ 6-962 H Cl H COOnC₃H₇ 6-963 F F H COOnC₃H₇ 6-964 F Cl H COOnC₃H₇ 6-965 Cl F H COOnC₃H₇ 6-966 Cl Cl H COOnC₃H₇ 6-967 H F H COOnC₄H₉ 6-968 H Cl H COOnC₄H₉ 6-969 F F H COOnC₄H₉ 6-970 F Cl H COOnC₄H₉ 6-971 Cl F H COOnC₄H₉ 6-972 Cl Cl H COOnC₄H₉ 6-973 H F H COOnC₅H₁₁ 6-974 H Cl H COOnC₅H₁₁ 6-975 F F H COOnC₅H₁₁

TABLE 102 X Y R¹ B 6-976 F Cl H COOnC₅H₁₁ 6-977 Cl F H COOnC₅H₁₁ 6-978 Cl Cl H COOnC₅H₁₁ 6-979 H F H COOiC₃H₇ 6-980 H Cl H COOiC₃H₇ 6-981 F F H COOiC₃H₇ 6-982 F Cl H COOiC₃H₇ 6-983 Cl F H COOiC₃H₇ 6-984 Cl Cl H COOiC₃H₇ 6-985 H F H COOcC₅H₉ 6-986 H Cl H COOcC₅H₉ 6-987 F F H COOcC₅H₉ 6-988 F Cl H COOcC₅H₉ 6-989 Cl F H COOcC₅H₉ 6-990 Cl Cl H COOcC₅H₉ 6-991 H F H COOcC₆H₁₁ 6-992 H Cl H COOcC₆H₁₁ 6-993 F F H COOcC₆H₁₁ 6-994 F Cl H COOcC₆H₁₁ 6-995 Cl F H COOcC₆H₁₁ 6-996 Cl Cl H COOcC₆H₁₁ 6-997 H F H COOCH₂C₆H₅ 6-998 H Cl H COOCH₂C₆H₅ 6-999 F F H COOCH₂C₆H₅ 6-1000 F Cl H COOCH₂C₆H₅

TABLE 103 X Y R¹ B 6-1001 Cl F H COOCH₂C₆H₅ 6-1002 Cl Cl H COOCH₂C₆H₅ 6-1003 H F H COOCH₂CH₂Cl 6-1004 H Cl H COOCH₂CH₂Cl 6-1005 F F H COOCH₂CH₂Cl 6-1006 F Cl H COOCH₂CH₂Cl 6-1007 Cl F H COOCH₂CH₂Cl 6-1008 Cl Cl H COOCH₂CH₂Cl 6-1009 H F H COOCH₂CH₂Br 6-1010 H Cl H COOCH₂CH₂Br 6-1011 F F H COOCH₂CH₂Br 6-1012 F Cl H COOCH₂CH₂Br 6-1013 Cl F H COOCH₂CH₂Br 6-1014 Cl Cl H COOCH₂CH₂Br 6-1015 H F H CONH₂ 6-1016 H Cl H CONH₂ 6-1017 F F H CONH₂ 6-1018 F Cl H CONH₂ 6-1019 Cl F H CONH₂ 6-1020 Cl Cl H CONH₂ 6-1021 H F H CONHCH₃ 6-1022 H Cl H CONHCH₃ 6-1023 F F H CONHCH₃ 6-1024 F Cl H CONHCH₃ 6-1025 Cl F H CONHCH₃

TABLE 104 X Y R¹ B 6-1026 Cl Cl H CONHCH₃ 6-1027 H F H CONHC₂H₅ 6-1028 H Cl H CONHC₂H₅ 6-1029 F F H CONHC₂H₅ 6-1030 F Cl H CONHC₂H₅ 6-1031 Cl F H CONHC₂H₅ 6-1032 Cl Cl H CONHC₂H₅ 6-1033 H F H CON(CH₃)₂ 6-1034 H Cl H CON(CH₃)₂ 6-1035 F F H CON(CH₃)₂ 6-1036 F Cl H CON(CH₃)₂ 6-1037 Cl F H CON(CH₃)₂ 6-1038 Cl Cl H CON(CH₃)₂ 6-1039 H F H CON(C₂H₅)₂ 6-1040 H Cl H CON(C₂H₅)₂ 6-1041 F F H CON(C₂H₅)₂ 6-1042 F Cl H CON(C₂H₅)₂ 6-1043 Cl F H CON(C₂H₅)₂ 6-1044 Cl Cl H CON(C₂H₅)₂ 6-1045 H F H CON(CH₃)(C₂H₅) 6-1046 H Cl H CON(CH₃)(C₂H₅) 6-1047 F F H CON(CH₃)(C₂H₅) 6-1048 F Cl H CON(CH₃)(C₂H₅) 6-1049 Cl F H CON(CH₃)(C₂H₅) 6-1050 Cl Cl H CON(CH₃)(C₂H₅)

TABLE 105 X Y R¹ B 6-1051 H F H COCH₃ 6-1052 H Cl H COCH₃ 6-1053 F F H COCH₃ 6-1054 F Cl H COCH₃ 6-1055 Cl F H COCH₃ 6-1056 Cl Cl H COCH₃ 6-1057 H F H COC₂H₅ 6-1058 H Cl H COC₂H₅ 6-1059 F F H COC₂H₅ 6-1060 F Cl H COC₂H₅ 6-1061 Cl F H COC₂H₅ 6-1062 Cl Cl H COC₂H₅ 6-1063 H F H COCH₂Cl 6-1064 H Cl H COCH₂Cl 6-1065 F F H COCH₂Cl 6-1066 F Cl H COCH₂Cl 6-1067 Cl F H COCH₂Cl 6-1068 Cl Cl H COCH₂Cl 6-1069 H F H CHO 6-1070 H Cl H CHO 6-1071 F F H CHO 6-1072 F Cl H CHO 6-1073 Cl F H CHO 6-1074 Cl Cl H CHO 6-1075 H F H CH₂CH₂COOH

TABLE 106 X Y R¹ B 6-1076 H Cl H CH₂CH₂COOH 6-1077 F F H CH₂CH₂COOH 6-1078 F Cl H CH₂CH₂COOH 6-1079 Cl F H CH₂CH₂COOH 6-1080 Cl Cl H CH₂CH₂COOH 6-1081 H F H CH₂CH₂COOCH₃ 6-1082 H Cl H CH₂CH₂COOCH₃ 6-1083 F F H CH₂CH₂COOCH₃ 6-1084 F Cl H CH₂CH₂COOCH₃ 6-1085 Cl F H CH₂CH₂COOCH₃ 6-1086 Cl Cl H CH₂CH₂COOCH₃ 6-1087 H F H CH₂CH₂COOC₂H₅ 6-1088 H Cl H CH₂CH₂COOC₂H₅ 6-1089 F F H CH₂CH₂COOC₂H₅ 6-1090 F Cl H CH₂CH₂COOC₂H₅ 6-1091 Cl F H CH₂CH₂COOC₂H₅ 6-1092 Cl Cl H CH₂CH₂COOC₂H₅ 6-1093 H F H CH₂CHClCOOCH₃ 6-1094 H Cl H CH₂CHClCOOCH₃ 6-1095 F F H CH₂CHClCOOCH₃ 6-1096 F Cl H CH₂CHClCOOCH₃ 6-1097 Cl F H CH₂CHClCOOCH₃ 6-1098 Cl Cl H CH₂CHClCOOCH₃ 6-1099 H F H CH₂CHClCOOC₂H₅ 6-1100 H Cl H CH₂CHClCOOC₂H₅

TABLE 107 X Y R¹ B 6-1101 F F H CH₂CHClCOOC₂H₅ 6-1102 F Cl H CH₂CHClCOOC₂H₅ 6-1103 Cl F H CH₂CHClCOOC₂H₅ 6-1104 Cl Cl H CH₂CHClCOOC₂H₅ 6-1105 H F H CH═CHCOOCH₃ 6-1106 H Cl H CH═CHCOOCH₃ 6-1107 F F H CH═CHCOOCH₃ 6-1108 F Cl H CH═CHCOOCH₃ 6-1109 Cl F H CH═CHCOOCH₃ 6-1110 Cl Cl H CH═CHCOOCH₃ 6-1111 H F H CH═CHCOOC₂H₅ 6-1112 H Cl H CH═CHCOOC₂H₅ 6-1113 F F H CH═CHCOOC₂H₅ 6-1114 F Cl H CH═CHCOOC₂H₅ 6-1115 Cl F H CH═CHCOOC₂H₅ 6-1116 Cl Cl H CH═CHCOOC₂H₅ 6-1117 H F H C(CH₃)═NOH 6-1118 H Cl H C(CH₃)═NOH 6-1119 F F H C(CH₃)═NOH 6-1120 F Cl H C(CH₃)═NOH 6-1121 Cl F H C(CH₃)═NOH 6-1122 Cl Cl H C(CH₃)═NOH 6-1123 H F H C(CH₃)═NOCH₃ 6-1124 H Cl H C(CH₃)═NOCH₃ 6-1125 F F H C(CH₃)═NOCH₃

TABLE 108 X Y R¹ B 6-1126 F Cl H C(CH₃)═NOCH₃ 6-1127 Cl F H C(CH₃)═NOCH₃ 6-1128 Cl Cl H C(CH₃)═NOCH₃ 6-1129 H F H C(CH₃)═NOC₂H₅ 6-1130 H Cl H C(CH₃)═NOC₂H₅ 6-1131 F F H C(CH₃)═NOC₂H₅ 6-1132 F Cl H C(CH₃)═NOC₂H₅ 6-1133 Cl F H C(CH₃)═NOC₂H₅ 6-1134 Cl Cl H C(CH₃)═NOC₂H₅ 6-1135 H F H C(CH₃)═NOiC₃H₇ 6-1136 H Cl H C(CH₃)═NOiC₃H₇ 6-1137 F F H C(CH₃)═NOiC₃H₇ 6-1138 F Cl H C(CH₃)═NOiC₃H₇ 6-1139 Cl F H C(CH₃)═NOiC₃H₇ 6-1140 Cl Cl H C(CH₃)═NOiC₃H₇ 6-1141 H F H C(CH₃)═NNH₂ 6-1142 H Cl H C(CH₃)═NNH₂ 6-1143 F F H C(CH₃)═NNH₂ 6-1144 F Cl H C(CH₃)═NNH₂ 6-1145 Cl F H C(CH₃)═NNH₂ 6-1146 Cl Cl H C(CH₃)═NNH₂ 6-1147 H F H C(CH₃)═NNHCH₃ 6-1148 H Cl H C(CH₃)═NNHCH₃ 6-1149 F F H C(CH₃)═NNHCH₃ 6-1150 F Cl H C(CH₃)═NNHCH₃

TABLE 109 X Y R¹ B 6-1151 Cl F H C(CH₃)═NNHCH₃ 6-1152 Cl Cl H C(CH₃)═NNHCH₃ 6-1153 H F H C(CH₃)═NN(CH₃)₂ 6-1154 H Cl H C(CH₃)═NN(CH₃)₂ 6-1155 F F H C(CH₃)═NN(CH₃)₂ 6-1156 F Cl H C(CH₃)═NN(CH₃)₂ 6-1157 Cl F H C(CH₃)═NN(CH₃)₂ 6-1158 Cl Cl H C(CH₃)═NN(CH₃)₂ 6-1159 H F H C(CH₃)═NNHC₂H₅ 6-1160 H Cl H C(CH₃)═NNHC₂H₅ 6-1161 F F H C(CH₃)═NNHC₂H₅ 6-1162 F Cl H C(CH₃)═NNHC₂H₅ 6-1163 Cl F H C(CH₃)═NNHC₂H₅ 6-1164 Cl Cl H C(CH₃)═NNHC₂H₅ 6-1165 H F H C(CH₃)═NN(C₂H₅)₂ 6-1166 H Cl H C(CH₃)═NN(C₂H₅)₂ 6-1167 F F H C(CH₃)═NN(C₂H₅)₂ 6-1168 F Cl H C(CH₃)═NN(C₂H₅)₂ 6-1169 Cl F H C(CH₃)═NN(C₂H₅)₂ 6-1170 Cl Cl H C(CH₃)═NN(C₂H₅)₂ 6-1171 H F H C(C₂H₅)═NNH₂ 6-1172 H Cl H C(C₂H₅)═NNH₂ 6-1173 F F H C(C₂H₅)═NNH₂ 6-1174 F Cl H C(C₂H₅)═NNH₂ 6-1175 Cl F H C(C₂H₅)═NNH₂

TABLE 110 X Y R¹ B 6-1176 Cl Cl H C(C₂H₅)═NNH₂ 6-1177 H F H C(C₂H₅)═NNHCH₃ 6-1178 H Cl H C(C₂H₅)═NNHCH₃ 6-1179 F F H C(C₂H₅)═NNHCH₃ 6-1180 F Cl H C(C₂H₅)═NNHCH₃ 6-1181 Cl F H C(C₂H₅)═NNHCH₃ 6-1182 Cl Cl H C(C₂H₅)═NNHCH₃ 6-1183 H F H C(C₂H₅)═NN(CH₃)₂ 6-1184 H Cl H C(C₂H₅)═NN(CH₃)₂ 6-1185 F F H C(C₂H₅)═NN(CH₃)₂ 6-1186 F Cl H C(C₂H₅)═NN(CH₃)₂ 6-1187 Cl F H C(C₂H₅)═NN(CH₃)₂ 6-1188 Cl Cl H C(C₂H₅)═NN(CH₃)₂ 6-1189 H F H C(C₂H₅)═NNHC₂H₅ 6-1190 H Cl H C(C₂H₅)═NNHC₂H₅ 6-1191 F F H C(C₂H₅)═NNHC₂H₅ 6-1192 F Cl H C(C₂H₅)═NNHC₂H₅ 6-1193 Cl F H C(C₂H₅)═NNHC₂H₅ 6-1194 Cl Cl H C(C₂H₅)═NNHC₂H₅ 6-1195 H F H C(C₂H₅)═NN(C₂H₅)₂ 6-1196 H Cl H C(C₂H₅)═NN(C₂H₅)₂ 6-1197 F F H C(C₂H₅)═NN(C₂H₅)₂ 6-1198 F Cl H C(C₂H₅)═NN(C₂H₅)₂ 6-1199 Cl F H C(C₂H₅)═NN(C₂H₅)₂ 6-1200 Cl Cl H C(C₂H₅)═NN(C₂H₅)₂

TABLE 111 X Y R¹ B 6-1201 H F H C(CH₃)(OCH₃)₂ 6-1202 H Cl H C(CH₃)(OCH₃)₂ 6-1203 F F H C(CH₃)(OCH₃)₂ 6-1204 F Cl H C(CH₃)(OCH₃)₂ 6-1205 Cl F H C(CH₃)(OCH₃)₂ 6-1206 Cl Cl H C(CH₃)(OCH₃)₂ 6-1207 H F H C(CH₃)(OC₂H₅)₂ 6-1208 H Cl H C(CH₃)(OC₂H₅)₂ 6-1209 F F H C(CH₃)(OC₂H₅)₂ 6-1210 F Cl H C(CH₃)(OC₂H₅)₂ 6-1211 Cl F H C(CH₃)(OC₂H₅)₂ 6-1212 Cl Cl H C(CH₃)(OC₂H₅)₂ 6-1213 H F H C(CH₃)(OiC₃H₇)₂ 6-1214 H Cl H C(CH₃)(OiC₃H₇)₂ 6-1215 F F H C(CH₃)(OiC₃H₇)₂ 6-1216 F Cl H C(CH₃)(OiC₃H₇)₂ 6-1217 Cl F H C(CH₃)(OiC₃H₇)₂ 6-1218 Cl Cl H C(CH₃)(OiC₃H₇)₂ 6-1219 H F H C(CH₃)(OCH₂CH₂O) 6-1220 H Cl H C(CH₃)(OCH₂CH₂O) 6-1221 F F H C(CH₃)(OCH₂CH₂O) 6-1222 F Cl H C(CH₃)(OCH₂CH₂O) 6-1223 Cl F H C(CH₃)(OCH₂CH₂O) 6-1224 Cl Cl H C(CH₃)(OCH₂CH₂O) 6-1225 H F H C(CH₃)(OCH₂CH₂CH₂O)

TABLE 112 X Y R¹ B 6-1226 H Cl H C(CH₃)(OCH₂CH₂CH₂O) 6-1227 F F H C(CH₃)(OCH₂CH₂CH₂O) 6-1228 F Cl H C(CH₃)(OCH₂CH₂CH₂O) 6-1229 Cl F H C(CH₃)(OCH₂CH₂CH₂O) 6-1230 Cl Cl H C(CH₃)(OCH₂CH₂CH₂O) 6-1231 H F H C(C₂H₅)(OCH₂CH₂O) 6-1232 H Cl H C(C₂H₅)(OCH₂CH₂O) 6-1233 F F H C(C₂H₅)(OCH₂CH₂O) 6-1234 F Cl H C(C₂H₅)(OCH₂CH₂O) 6-1235 Cl F H C(C₂H₅)(OCH₂CH₂O) 6-1236 Cl Cl H C(C₂H₅)(OCH₂CH₂O) 6-1237 H F H C(C₂H₅)(OCH₂CH₂CH₂O) 6-1238 H Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 6-1239 F F H C(C₂H₅)(OCH₂CH₂CH₂O) 6-1240 F Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 6-1241 Cl F H C(C₂H₅)(OCH₂CH₂CH₂O) 6-1242 Cl Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 6-1243 H F H OCH₂CH(CH₃)₂ 6-1244 H Cl H OCH₂CH(CH₃)₂ 6-1245 F F H OCH₂CH(CH₃)₂ 6-1246 F Cl H OCH₂CH(CH₃)₂ 6-1247 Cl F H OCH₂CH(CH₃)₂ 6-1248 Cl Cl H OCH₂CH(CH₃)₂ 6-1249 H F H OCH₂CH₂F 6-1250 H Cl H OCH₂CH₂F

TABLE 113 X Y R¹ B 6-1251 F F H OCH₂CH₂F 6-1252 F Cl H OCH₂CH₂F 6-1253 Cl F H OCH₂CH₂F 6-1254 Cl Cl H OCH₂CH₂F 6-1255 H Cl H CH₂OH 6-1256 F Cl H CH₂OH 6-1257 H Cl H CH₂OCOCH₃ 6-1258 F Cl H CH₂OCOCH₃

Compounds of the general formula:

TABLE 114 X Z¹ n R¹ R⁴ R⁵ 7-1 H O 1 H H H 7-2  F O 1 H H H 7-3  H O 1 H H CH₃ 7-4  F O 1 H H CH₃ 7-5  H O 1 H H C₂H₅ 7-6  F O 1 H H C₂H₅ 7-7  H O 1 H H nC₃H₇ 7-8  F O 1 H H nC₃H₇ 7-9  H O 1 H H nC₄H₉ 7-10 F O 1 H H nC₄H₉ 7-11 H O 1 H H nC₅H₁₁ 7-12 F O 1 H H nC₅H₁₁ 7-13 H O 1 H H iC₃H₇ 7-14 F O 1 H H iC₃H₇ 7-15 H O 1 H H CH₂CH₂Cl 7-16 F O 1 H H CH₂CH₂Cl 7-17 H O 1 H H CH₂CH₂Br 7-18 F O 1 H H CH₂CH₂Br 7-19 H O 1 H H CH₂CH═CH₂ 7-20 F O 1 H H CH₂CH═CH₂ 7-21 H O 1 H H CH(CH₃)CH═CH₂ 7-22 F O 1 H H CH(CH₃)CH═CH₂ 7-23 H O 1 H H CH₂CCl═CH₂ 7-24 F O 1 H H CH₂CCl═CH₂ 7-25 H O 1 H H CH₂C≡CH

TABLE 115 X Z¹ n R¹ R⁴ R⁵ 7-26 F O 1 H H CH₂C≡CH 7-27 H O 1 H H CH(CH₃)C≡CH 7-28 F O 1 H H CH(CH₃)C≡CH 7-29 H O 1 H H CH₂CN 7-30 F O 1 H H CH₂CN 7-31 H O 1 H H CH₂OCH₃ 7-32 F O 1 H H CH₂OCH₃ 7-33 H O 1 H H CH₂OC₂H₅ 7-34 F O 1 H H CH₂OC₂H₅ 7-35 H O 1 H H CH₂COOH 7-36 F O 1 H H CH₂COOH 7-37 H O 1 H H CH₂COOCH₃ 7-38 F O 1 H H CH₂COOCH₃ 7-39 H O 1 H H CH₂COOC₂H₅ 7-40 F O 1 H H CH₂COOC₂H₅ 7-41 H O 1 H H CH₂COOnC₃H₇ 7-42 F O 1 H H CH₂COOnC₃H₇ 7-43 H O 1 H H CH₂COOnC₄H₉ 7-44 F O 1 H H CH₂COOnC₄H₉ 7-45 H O 1 H H CH₂COOnC₅H₁₁ 7-46 F O 1 H H CH₂COOnC₅H₁₁ 7-47 H O 1 H H CH₂COOiC₃H₇ 7-48 F O 1 H H CH₂COOiC₃H₇ 7-49 H O 1 H H CH₂COOcC₅H₉ 7-50 F O 1 H H CH₂COOcC₅H₉

TABLE 116 X Z¹ n R¹ R⁴ R⁵ 7-51 H O 1 H H CH₂COOcC₆H₁₁ 7-52 F O 1 H H CH₂COOcC₆H₁₁ 7-53 H O 1 H H CH(CH₃)COOH 7-54 F O 1 H H CH(CH₃)COOH 7-55 H O 1 H H CH(CH₃)COOCH₃ 7-56 F O 1 H H CH(CH₃)COOCH₃ 7-57 H O 1 H H CH(CH₃)COOC₂H₅ 7-58 F O 1 H H CH(CH₃)COOC₂H₅ 7-59 H O 1 H H CH(CH₃)COOnC₃H₇ 7-60 F O 1 H H CH(CH₃)COOnC₃H₇ 7-61 H O 1 H H CH(CH₃)COOnC₄H₉ 7-62 F O 1 H H CH(CH₃)COOnC₄H₉ 7-63 H O 1 H H CH(CH₃)COOnC₅H₁₁ 7-64 F O 1 H H CH(CH₃)COOnC₅H₁₁ 7-65 H O 1 H H CH(CH₃)COOiC₃H₇ 7-66 F O 1 H H CH(CH₃)COOiC₃H₇ 7-67 H O 1 H H CH(CH₃)COOcC₅H₉ 7-68 F O 1 H H CH(CH₃)COOcC₅H₉ 7-69 H O 1 H H CH(CH₃)COOcC₆H₁₁ 7-70 F O 1 H H CH(CH₃)COOcC₆H₁₁ 7-71 H O 1 H CH₃ H 7-72 F O 1 H CH₃ H 7-73 H O 1 H CH₃ CH₃ 7-74 F O 1 H CH₃ CH₃ 7-75 H O 1 H CH₃ C₂H₅

TABLE 117 X Z¹ n R¹ R⁴ R⁵ 7-76 F O 1 H CH₃ C₂H₅ 7-77 H O 1 H CH₃ nC₃H₇ 7-78 F O 1 H CH₃ nC₃H₇ 7-79 H O 1 H CH₃ nC₄H₉ 7-80 F O 1 H CH₃ nC₄H₉ 7-81 H O 1 H CH₃ nC₅H₁₁ 7-82 F O 1 H CH₃ nC₅H₁₁ 7-83 H O 1 H CH₃ iC₃H₇ 7-84 F O 1 H CH₃ iC₃H₇ 7-85 H O 1 H CH₃ CH₂CH₂Cl 7-86 F O 1 H CH₃ CH₂CH₂Cl 7-87 H O 1 H CH₃ CH₂CH₂Br 7-88 F O 1 H CH₃ CH₂CH₂Br 7-89 H O 1 H CH₃ CH₂CH═CH₂ 7-90 F O 1 H CH₃ CH₂CH═CH₂ 7-91 H O 1 H CH₃ CH(CH₃)CH═CH₂ 7-92 F O 1 H CH₃ CH(CH₃)CH═CH₂ 7-93 H O 1 H CH₃ CH₂CCl═CH₂ 7-94 F O 1 H CH₃ CH₂CCl═CH₂ 7-95 H O 1 H CH₃ CH₂C≡CH 7-96 F O 1 H CH₃ CH₂C≡CH 7-97 H O 1 H CH₃ CH(CH₃)C≡CH 7-98 F O 1 H CH₃ CH(CH₃)C≡CH 7-99 H O 1 H CH₃ CH₂CN  7-100 F O 1 H CH₃ CH₂CN

TABLE 118 X Z¹ n R¹ R⁴ R⁵ 7-101 H O 1 H CH₃ CH₂OCH₃ 7-102 F O 1 H CH₃ CH₂OCH₃ 7-103 H O 1 H CH₃ CH₂OC₂H₅ 7-104 F O 1 H CH₃ CH₂OC₂H₅ 7-105 H O 0 H — H 7-106 F O 0 H — H 7-107 H O 0 H — CH₃ 7-108 F O 0 H — CH₃ 7-109 H O 0 H — C₂H₅ 7-110 F O 0 H — C₂H₅ 7-111 H O 0 H — nC₃H₇ 7-112 F O 0 H — nC₃H₇ 7-113 H O 0 H — nC₄H₉ 7-114 F O 0 H — nC₄H₉ 7-115 H O 0 H — nC₅H₁₁ 7-116 F O 0 H — nC₅H₁₁ 7-117 H O 0 H — iC₃H₇ 7-118 F O 0 H — iC₃H₇ 7-119 H O 0 H — CH₂CH₂Cl 7-120 F O 0 H — CH₂CH₂Cl 7-121 H O 0 H — CH₂CH₂Br 7-122 F O 0 H — CH₂CH₂Br 7-123 H O 0 H — CH₂CH═CH₂ 7-124 F O 0 H — CH₂CH═CH₂ 7-125 H O 0 H — CH(CH₃)CH═CH₂

TABLE 119 X Z¹ n R¹ R⁴ R⁵ 7-126 F O 0 H — CH(CH₃)CH═CH₂ 7-127 H O 0 H — CH₂CCl═CH₂ 7-128 F O 0 H — CH₂CCl═CH₂ 7-129 H O 0 H — CH₂C≡CH 7-130 F O 0 H — CH₂C≡CH 7-131 H O 0 H — CH(CH₃)C≡CH 7-132 F O 0 H — CH(CH₃)C≡CH 7-133 H O 0 H — CH₂CN 7-134 F O 0 H — CH₂CN 7-135 H O 0 H — CH₂OCH₃ 7-136 F O 0 H — CH₂OCH₃ 7-137 H O 0 H — CH₂OC₂H₅ 7-138 F O 0 H — CH₂OC₂H₅ 7-139 H S 0 H — H 7-140 F S 0 H — H 7-141 H S 0 H — CH₃ 7-142 F S 0 H — CH₃ 7-143 H S 0 H — C₂H₅ 7-144 F S 0 H — C₂H₅ 7-145 H S 0 H — nC₃H₇ 7-146 F S 0 H — nC₃H₇ 7-147 H S 0 H — nC₄H₉ 7-148 F S 0 H — nC₄H₉ 7-149 H S 0 H — nC₅H₁₁ 7-150 F S 0 H — nC₅H₁₁

TABLE 120 X Z¹ n R¹ R⁴ R⁵ 7-151 H S 0 H — iC₃H₇ 7-152 F S 0 H — iC₃H₇ 7-153 H S 0 H — CH₂CH₂Cl 7-154 F S 0 H — CH₂CH₂Cl 7-155 H S 0 H — CH₂CH₂Br 7-156 F S 0 H — CH₂CH₂Br 7-157 H S 0 H — CH₂CH═CH₂ 7-158 F S 0 H — CH₂CH═CH₂ 7-159 H S 0 H — CH(CH₃)CH═CH₂ 7-160 F S 0 H — CH(CH₃)CH═CH₂ 7-161 H S 0 H — CH₂CCl═CH₂ 7-162 F S 0 H — CH₂CCl═CH₂ 7-163 H S 0 H — CH₂C≡CH 7-164 F S 0 H — CH₂C≡CH 7-165 H S 0 H — CH(CH₃)C≡CH 7-166 F S 0 H — CH(CH₃)C≡CH 7-167 H S 0 H — CH₂CN 7-168 F S 0 H — CH₂CN 7-169 H S 0 H — CH₂OCH₃ 7-170 F S 0 H — CH₂OCH₃ 7-171 H S 0 H — CH₂OC₂H₅ 7-172 F S 0 H — CH₂OC₂H₅ 7-173 H S 0 H — CH₂COOH 7-174 F S 0 H — CH₂COOH 7-175 H S 0 H — CH₂COOCH₃

TABLE 121 X Z¹ n R¹ R⁴ R⁵ 7-176 F S 0 H — CH₂COOCH₃ 7-177 H S 0 H — CH₂COOC₂H₅ 7-178 F S 0 H — CH₂COOC₂H₅ 7-179 H S 0 H — CH₂COOnC₃H₇ 7-180 F S 0 H — CH₂COOnC₃H₇ 7-181 H S 0 H — CH₂COOnC₄H₉ 7-182 F S 0 H — CH₂COOnC₄H₉ 7-183 H S 0 H — CH₂COOnC₅H₁₁ 7-184 F S 0 H — CH₂COOnC₅H₁₁ 7-185 H S 0 H — CH₂COOiC₃H₇ 7-186 F S 0 H — CH₂COOiC₃H₇ 7-187 H S 0 H — CH₂COOcC₅H₉ 7-188 F S 0 H — CH₂COOcC₅H₉ 7-189 H S 0 H — CH₂COOcC₆H11 7-190 F S 0 H — CH₂COOcC₆H₁₁ 7-191 H S 0 H — CH(CH₃)COOH 7-192 F S 0 H — CH(CH₃)COOH 7-193 H S 0 H — CH(CH₃)COOCH₃ 7-194 F S 0 H — CH(CH₃)COOCH₃ 7-195 H S 0 H — CH(CH₃)COOC₂H₅ 7-196 F S 0 H — CH(CH₃)COOC₂H₅ 7-197 H S 0 H — CH(CH₃)COOnC₃H₇ 7-198 F S 0 H — CH(CH₃)COOnC₃H₇ 7-199 H S 0 H — CH(CH₃)COOnC₄H₉ 7-200 F S 0 H — CH(CH₃)COOnC₄H₉

TABLE 122 X Z¹ n R¹ R⁴ R⁵ 7-201 H S 0 H — CH(CH₃)COOnC₅H₁₁ 7-202 F S 0 H — CH(CH₃)COOnC₅H₁₁ 7-203 H S 0 H — CH(CH₃)COOiC₃H₇ 7-204 F S 0 H — CH(CH₃)COOiC₃H₇ 7-205 H S 0 H — CH(CH₃)COOcC₅H₉ 7-206 F S 0 H — CH(CH₃)COOcC₅H₉ 7-207 H S 0 H — CH(CH₃)COOcC₆H₁₁ 7-208 F S 0 H — CH(CH₃)COOcC₆H₁₁

Compounds of the general formula:

TABLE 123 X R¹ R⁵ 10-1  H H CH₃ 10-2  F H CH₃ 10-3  Cl H CH₃ 10-4  H H C₂H₅ 10-5  F H C₂H₅ 10-6  Cl H C₂H₅ 10-7  H H nC₃H₇ 10-8  F H nC₃H₇ 10-9  Cl H nC₃H₇ 10-10 H H nC₄H₉ 10-11 F H nC₄H₉ 10-12 Cl H nC₄H₉ 10-13 H H iC₄H₉ 10-14 F H iC₄H₉ 10-15 Cl H iC₄H₉ 10-16 H H CH₂CH═CH₂ 10-17 F H CH₂CH═CH₂ 10-18 Cl H CH₂CH═CH₂ 10-19 H H CH(CH₃)CH═CH₂ 10-20 F H CH(CH₃)CH═CH₂ 10-21 Cl H CH(CH₃)CH═CH₂ 10-22 H H CH₂C≡CH 10-23 F H CH₂C≡CH 10-24 Cl H CH₂C≡CH 10-25 H H CH(CH₃)C≡CH

TABLE 124 X R¹ R⁵ 10-26 F H CH(CH₃)C≡CH 10-27 Cl H CH(CH₃)C≡CH

Compounds of the general formula:

TABLE 125 X Y R¹ B 11-1  H F H H 11-2  H Cl H H 11-3  H Br H H 11-4  F F H H 11-5  F Cl H H 11-6  F Br H H 11-7  Cl F H H 11-8  Cl Cl H H 11-9  Cl Br H H 11-10 H F H NO₂ 11-11 H Cl H NO₂ 11-12 H Br H NO₂ 11-13 F F H NO₂ 11-14 F Cl H NO₂ 11-15 F Br H NO₂ 11-16 Cl F H NO₂ 11-17 Cl Cl H NO₂ 11-18 Cl Br H NO₂ 11-19 H F H NH₂ 11-20 H Cl H NH₂ 11-21 H Br H NH₂ 11-22 F F H NH₂ 11-23 F CL H NH₂ 11-24 F Br H NH₂ 11-25 Cl F H NH₂

TABLE 126 X Y R¹ B 11-26 Cl Cl H NH₂ 11-27 Cl Br H NH₂ 11-28 H F H OH 11-29 H Cl H OH 11-30 H Br H OH 11-31 F F H OH 11-32 F Cl H OH 11-33 F Br H OH 11-34 Cl F H OH 11-35 Cl Cl H OH 11-36 Cl Br H OH 11-37 H F H SH 11-38 H Cl H SH 11-39 H Br H SH 11-40 F F H SH 11-41 F Cl H SH 11-42 F Br H SH 11-43 Cl F H SH 11-44 Cl Cl H SH 11-45 Cl Br H SH 11-46 H F H SO₂Cl 11-47 H Cl H SO₂Cl 11-48 H Br H SO₂Cl 11-49 F F H SO₂Cl 11-50 F Cl H SO₂Cl

TABLE 127 X Y R¹ B 11-51 F Br H SO₂Cl 11-52 Cl F H SO₂Cl 11-53 Cl Cl H SO₂Cl 11-54 Cl Br H SO₂Cl 11-55 H F H NHCH₃ 11-56 H Cl H NHCH₃ 11-57 F F H NHCH₃ 11-58 F Cl H NHCH₃ 11-59 Cl F H NHCH₃ 11-60 Cl Cl H NHCH₃ 11-61 H F W NHC₂H₅ 11-62 H Cl H NHC₂H₅ 11-63 F F H NHC₂H₅ 11-64 F Cl H NHC₂H₅ 11-65 Cl F H NHC₂H₅ 11-66 Cl Cl H NHC₂H₅ 11-67 H F H NHCH₂CH═CH₂ 11-68 H Cl H NHCH₂CH═CH₂ 11-69 F F H NHCH₂CH═CH₂ 11-70 F Cl H NHCH₂CH═CH₂ 11-71 Cl F H NHCH₂CH═CH₂ 11-72 Cl Cl H NHCH₂CH═CH₂ 11-73 H F H NHCH₂C≡CH 11-74 H Cl H NHCH₂C≡CH 11-75 F F H NHCH₂C≡CH

TABLE 128 X Y R¹ B 11-76 F Cl H NHCH₂C≡CH 11-77 Cl F H NHCH₂C≡CH 11-78 Cl Cl H NHCH₂C≡CH 11-79 H F H NHCH(CH₃)C≡CH 11-80 H Cl H NHCH(CH₃)C≡CH 11-81 F F H NHCH(CH₃)C≡CH 11-82 F Cl H NHCH(CH₃)C≡CH 11-83 Cl F H NHCH(CH₃)C≡CH 11-84 Cl Cl H NHCH(CH₃)C≡CH 11-85 H F H NHSO₂CH₃ 11-86 H Cl H NHSO₂CH₃ 11-87 F F H NHSO₂CH₃ 11-88 F Cl H NHSO₂CH₃ 11-89 Cl F H NHSO₂CH₃ 11-90 Cl Cl H NHSO₂CH₃ 11-91 H F H NHSO₂C₂H₅ 11-92 H Cl H NHSO₂C₂H₅ 11-93 F F H NHSO₂C₂H₅ 11-94 F Cl H NHSO₂C₂H₅ 11-95 Cl F H NHSO₂C₂H₅ 11-96 Cl Cl H NHSO₂C₂H₅ 11-97 H F H NHSO₂CH₂Cl 11-98 H Cl H NHSO₂CH₂Cl 11-99 F F H NHSO₂CH₂Cl  11-100 F Cl H NHSO₂CH₂Cl

TABLE 129 X Y R¹ B 11-101 Cl F H NHSO₂CH₂Cl 11-102 Cl Cl H NHSO₂CH₂Cl 11-103 H F H NHSO₂CF₃ 11-104 H Cl H NHSO₂CF₃ 11-105 F F H NHSO₂CF₃ 11-106 F Cl H NHSO₂CF₃ 11-107 Cl F H NHSO₂CF₃ 11-108 Cl Cl H NHSO₂CF₃ 11-109 H F H N(SO₂CH₃)₂ 11-110 H Cl H N(SO₂CH₃)₂ 11-111 F F H N(SO₂CH₃)₂ 11-112 F Cl H N(SO₂CH₃)₂ 11-113 Cl F H N(SO₂CH₃)₂ 11-114 Cl CL H N(SO₂CH₃)₂ 11-115 H F H N(CH₃)SO₂CH₃ 11-116 H Cl H N(CH₃)SO₂CH₃ 11-117 F F H N(CH₃)SO₂CH₃ 11-118 F Cl H N(CH₃)SO₂CH₃ 11-119 Cl F H N(CH₃)SO₂CH₃ 11-120 Cl Cl H N(CH₃)SO₂CH₃ 11-121 H F H N(CH₂C≡CH)SO₂CH₃ 11-122 H Cl H N(CH₂C≡CH)SO₂CH₃ 11-123 F F H N(CH₂C≡CH)SO₂CH₃ 11-124 F Cl H N(CH₂C≡CH)SO₂CH₃ 11-125 Cl F H N(CH₂C≡CH)SO₂CH₃

TABLE 130 X Y R¹ B 11-126 Cl Cl H N(CH₂C≡CH)SO₂CH₃ 11-127 H F H NHCOOCH₃ 11-128 H Cl H NHCOOCH₃ 11-129 F F H NHCOOCH₃ 11-130 F Cl H NHCOOCH₃ 11-131 Cl F H NHCOOCH₃ 11-132 Cl Cl H NHCOOCH₃ 11-133 H F H NHCOOC₂H₅ 11-134 H Cl H NHCOOC₂H₅ 11-135 F F H NHCOOC₂H₅ 11-136 F Cl H NHCOOC₂H₅ 11-137 Cl F H NHCOOC₂H₅ 11-138 Cl Cl H NHCOOC₂H₅ 11-139 H F H NHCOOnC₃H₇ 11-140 H Cl H NHCOOnC₃H₇ 11-141 F F H NHCOOnC₃H₇ 11-142 F Cl H NHCOOnC₃H₇ 11-143 Cl F H NHCOOnC₃H₇ 11-144 Cl Cl H NHCOOnC₃H₇ 11-145 H F H NHCOOiC₃H₇ 11-146 H Cl H NHCOOiC₃H₇ 11-147 F F H NHCOOiC₃H₇ 11-148 F Cl H NHCOOiC₃H₇ 11-149 Cl F H NHCOOiC₃H₇ 11-150 Cl Cl H NHCOOiC₃H₇

TABLE 131 X Y R¹ B 11-151 H F H NHCOOnC₄H₉ 11-152 H Cl H NHCOOnC₄H₉ 11-153 F F H NHCOOnC₄H₉ 11-154 F Cl H NHCOOnC₄H₉ 11-155 Cl F H NHCOOnC₄H₉ 11-156 Cl Cl H NHCOOnC₄H₉ 11-157 H F H NHCOOnC₅H₁₁ 11-158 H Cl H NHCOOnC₅H₁₁ 11-159 F F H NHCOOnC₅H₁₁ 11-160 F Cl H NHCOOnC₅H₁₁ 11-161 Cl F H NHCOOnC₅H₁₁ 11-162 Cl Cl H NHCOOnC₅H₁₁ 11-163 H F H NHCH₂COOCH₃ 11-164 H Cl H NHCH₂COOCH₃ 11-165 F F H NHCH₂COOCH₃ 11-166 F Cl H NHCH₂COOCH₃ 11-167 Cl F H NHCH₂COOCH₃ 11-168 Cl Cl H NHCH₂COOCH₃ 11-169 H F H NHCH₂COOC₂H₅ 11-170 H Cl H NHCH₂COOC₂H₅ 11-171 F F H NHCH₂COOC₂H₅ 11-172 F Cl H NHCH₂COOC₂H₅ 11-173 Cl F H NHCH₂COOC₂H₅ 11-174 Cl Cl H NHCH₂COOC₂H₅ 11-175 H F H NHCH₂COOnC₃H₇

TABLE 132 X Y R¹ B 11-176 H Cl H NHCH₂COOnC₃H₇ 11-177 F F H NHCH₂COOnC₃H₇ 11-178 F Cl H NHCH₂COOnC₃H₇ 11-179 Cl F H NHCH₂COOnC₃H₇ 11-180 Cl Cl H NHCH₂COOnC₃H₇ 11-181 H F H NHCH₂COOnC₄H₉ 11-182 H Cl H NHCH₂COOnC₄H₉ 11-183 F F H NHCH₂COOnC₄H₉ 11-184 F Cl H NHCH₂COOnC₄H₉ 11-185 Cl F H NHCH₂COOnC₄H₉ 11-186 Cl Cl H NHCH₂COOnC₄H₉ 11-187 H F H NHCH₂COOnC₅H₁₁ 11-188 H Cl H NHCH₂COOnC₅H₁₁ 11-189 F F H NHCH₂COOnC₅H₁₁ 11-190 F Cl H NHCH₂COOnC₅H₁₁ 11-191 Cl F H NHCH₂COOnC₅H₁₁ 11-192 Cl Cl H NHCH₂COOnC₅H₁₁ 11-193 H F H NHCH₂COOiC₃H₇ 11-194 H Cl H NHCH₂COOiC₃H₇ 11-195 F F H NHCH₂COOiC₃H₇ 11-196 F Cl H NHCH₂COOiC₃H₇ 11-197 Cl F H NHCH₂COOiC₃H₇ 11-198 Cl Cl H NHCH₂COOiC₃H₇ 11-199 H F H NHCH₂COOcC₅H₉ 11-200 H Cl H NHCH₂COOcC₅H₉

TABLE 133 X Y R¹ B 11-201 F F H NHCH₂COOcC₅H₉ 11-202 F Cl H NHCH₂COOcC₅H₉ 11-203 Cl F H NHCH₂COOcC₅H₉ 11-204 Cl Cl H NHCH₂COOcC₅H₉ 11-205 H F H NHCH₂COOcC₆H₁₁ 11-206 H Cl H NHCH₂COOcC₆H₁₁ 11-207 F F H NHCH₂COOcC₆H₁₁ 11-208 F Cl H NHCH₂COOcC₆H₁₁ 11-209 Cl F H NHCH₂COOcC₆H₁₁ 11-210 Cl Cl H NHCH₂COOcC₆H₁₁ 11-211 H F H NHCH(CH₃)COOCH₃ 11-212 H Cl H NHCH(CH₃)COOCH₃ 11-213 F F H NHCH(CH₃)COOCH₃ 11-214 F Cl H NHCH(CH₃)COOCH₃ 11-215 Cl F H NHCH(CH₃)COOCH₃ 11-216 Cl Cl H NHCH(CH₃)COOCH₃ 11-217 H F H NHCH(CH₃)COOC₂H₅ 11-218 H Cl H NHCH(CH₃)COOC₂H₅ 11-219 F F H NHCH(CH₃)COOC₂H₅ 11-220 F Cl H NHCH(CH₃)COOC₂H₅ 11-221 Cl F H NHCH(CH₃)COOC₂H₅ 11-222 Cl Cl H NHCH(CH₃)COOC₂H₅ 11-223 H F H NHCH(CH₃)COOnC₃H₇ 11-224 H Cl H NHCH(CH₃)COOnC₃H₇ 11-225 F F H NHCH(CH₃)COOnC₃H₇

TABLE 134 X Y R¹ B 11-226 F Cl H NHCH(CH₃)COOnC₃H₇ 11-227 Cl F H NHCH(CH₃)COOnC₃H₇ 11-228 Cl Cl H NHCH(CH₃)COOnC₃H₇ 11-229 H F H NHCH(CH₃)COOnC₄H₉ 11-230 H Cl H NHCH(CH₃)COOnC₄H₉ 11-231 F F H NHCH(CH₃)COOnC₄H₉ 11-232 F Cl H NHCH(CH₃)COOnC₄H₉ 11-233 Cl F H NHCH(CH₃)COOnC₄H₉ 11-234 Cl Cl H NHCH(CH₃)COOnC₄H₉ 11-235 H F H NHCH(CH₃)COOnC₅H₁₁ 11-236 H Cl H NHCH(CH₃)COOnC₅H₁₁ 11-237 F F H NHCH(CH₃)COOnC₅H₁₁ 11-238 F Cl H NHCH(CH₃)COOnC₅H₁₁ 11-239 Cl F H NHCH(CH₃)COOnC₅H₁₁ 11-240 Cl Cl H NHCH(CH₃)COOnC₅H₁₁ 11-241 H F H NHCH(CH₃)COOiC₃H₇ 11-242 H Cl H NHCH(CH₃)COOiC₃H₇ 11-243 F F H NHCH(CH₃)COOiC₃H₇ 11-244 F Cl H NHCH(CH₃)COOiC₃H₇ 11-245 Cl F H NHCH(CH₃)COOiC₃H₇ 11-246 Cl Cl H NHCH(CH₃)COOiC₃H₇ 11-247 H F H NHCH(CH₃)COOcC₅H₉ 11-248 H Cl H NHCH(CH₃)COOcC₅H₉ 11-249 F F H NHCH(CH₃)COOcC₅H₉ 11-250 F Cl H NHCH(CH₃)COOcC₅H₉

TABLE 135 X Y R¹ B 11-251 Cl F H NHCH(CH₃)COOcC₅H₉ 11-252 Cl Cl H NHCH(CH₃)COOcC₅H₉ 11-253 H F H NHCH(CH₃)COOcC₆H₁₁ 11-254 H Cl H NHCH(CH₃)COOcC₆H₁₁ 11-255 F F H NHCH(CH₃)COOcC₆H₁₁ 11-256 F Cl H NHCH(CH₃)COOcC₆H₁₁ 11-257 Cl F H NHCH(CH₃)COOcC₆H₁₁ 11-258 Cl Cl H NHCH(CH₃)COOcC₆H₁₁ 11-259 H F H OCH₃ 11-260 H Cl H OCH₃ 11-261 F F H OCH₃ 11-262 F Cl H OCH₃ 11-263 Cl F H OCH₃ 11-264 Cl Cl H OCH₃ 11-265 H F H OC₂H₅ 11-266 H Cl H OC₂H₅ 11-267 F F H OC₂H₅ 11-268 F Cl H OC₂H₅ 11-269 Cl F H OC₂H₅ 11-270 Cl Cl H OC₂H₅ 11-271 H F H OiC₃H₇ 11-272 H Cl H OiC₃H₇ 11-273 F F H OiC₃H₇ 11-274 F Cl H OiC₃H₇ 11-275 Cl F H OiC₃H₇

TABLE 136 X Y R¹ B 11-276 Cl Cl H OiC₃H₇ 11-277 H F H OnC₃H₇ 11-278 H Cl H OnC₃H₇ 11-279 F F H OnC₃H₇ 11-280 F Cl H OnC₃H₇ 11-281 Cl F H OnC₃H₇ 11-282 Cl Cl H OnC₃H₇ 11-283 H F H OCH₂CH₂Cl 11-284 H Cl H OCH₂CH₂Cl 11-285 F F H OCH₂CH₂Cl 11-286 F Cl H OCH₂CH₂Cl 11-287 Cl F H OCH₂CH₂Cl 11-288 Cl Cl H OCH₂CH₂Cl 11-289 H F H OCF₂CF₂H 11-290 H Cl H OCF₂CF₂H 11-291 F F H OCF₂CF₂H 11-292 F Cl H OCF₂CF₂H 11-293 Cl F H OCF₂CF₂H 11-294 Cl Cl H OCF₂CF₂H 11-295 H F H OcC₅H₉ 11-296 H Cl H OcC₅H₉ 11-297 F F H OcC₅H₉ 11-298 F Cl H OcC₅H₉ 11-299 Cl F H OcC₅H₉ 11-300 Cl Cl H OcC₅H₉

TABLE 137 X Y R¹ B 11-301 H F H OcC₆H₁₁ 11-302 H Cl H OcC₆H₁₁ 11-303 F F H OcC₆H₁₁ 11-304 F Cl H OcC₆H₁₁ 11-305 Cl F H OcC₆H₁₁ 11-306 Cl Cl H OcC₆H₁₁ 11-307 H F H OCH₂CH═CH₂ 11-308 H Cl H OCH₂CH═CH₂ 11-309 F F H OCH₂CH═CH₂ 11-310 F Cl H OCH₂CH═CH₂ 11-311 Cl F H OCH₂CH═CH₂ 11-312 Cl Cl H OCH₂CH═CH₂ 11-313 H F H OCH₂CCl═CH₂ 11-314 H Cl H OCH₂CCl═CH₂ 11-315 F F H OCH₂CCl═CH₂ 11-316 F Cl H OCH₂CCl═CH₂ 11-317 Cl F H OCH₂CCl═CH₂ 11-318 Cl Cl H OCH₂CCl═CH₂ 11-319 H F H OCH₂CCl═CHCl 11-320 H Cl H OCH₂CCl═CHCl 11-321 F F H OCH₂CCl═CHCl 11-322 F Cl H OCH₂CCl═CHCl 11-323 Cl F H OCH₂CCl═CHCl 11-324 Cl Cl H OCH₂CCl═CHCl 11-325 H F H OCH(CH₃)CH═CH₂

TABLE 138 X Y R¹ B 11-326 H Cl H OCH(CH₃)CH═CH₂ 11-327 F F H OCH(CH₃)CH═CH₂ 11-328 F Cl H OCH(CH₃)CH═CH₂ 11-329 Cl F H OCH(CH₃)CH═CH₂ 11-330 Cl Cl H OCH(CH₃)CH═CH₂ 11-331 H F H OCH₂C(CH₃)═CH₂ 11-332 H Cl H OCH₂C(CH₃)═CH₂ 11-333 F F H OCH₂C(CH₃)═CH₂ 11-334 F Cl H OCH₂C(CH₃)═CH₂ 11-335 Cl F H OCH₂C(CH₃)═CH₂ 11-336 Cl Cl H OCH₂C(CH₃)═CH₂ 11-337 H F H OCH₂C≡CH 11-338 H Cl H OCH₂C≡CH 11-339 F F H OCH₂C≡CH 11-340 F Cl H OCH₂C≡CH 11-341 Cl F H OCH₂C≡CH 11-342 Cl Cl H OCH₂C≡CH 11-343 H F H OCH(CH₃)C≡CH 11-344 H Cl H OCH(CH₃)C≡CH 11-345 F F H OCH(CH₃)C≡CH 11-346 F Cl H OCH(CH₃)C≡CH 11-347 Cl F H OCH(CH₃)C≡CH 11-348 Cl Cl H OCH(CH₃)C≡CH 11-349 H F H OCH₂C≡CBr 11-350 H Cl H OCH₂C≡CBr

TABLE 139 X Y R¹ B 11-351 F F H OCH₂C≡CBr 11-352 F Cl H OCH₂C≡CBr 11-353 Cl F H OCH₂C≡CBr 11-354 Cl Cl H OCH₂C≡CBr 11-355 H F H OCH₂C≡CCl 11-356 H Cl H OCH₂C≡CCl 11-357 F F H OCH₂C≡CCl 11-358 F Cl H OCH₂C≡CCl 11-359 Cl F H OCH₂C≡CCl 11-360 Cl Cl H OCH₂C≡CCl 11-361 H F H OCH₂C≡CCH₂Cl 11-362 H Cl H OCH₂C≡CCH₂Cl 11-363 F F H OCH₂C≡CCH₂Cl 11-364 F Cl H OCH₂C≡CCH₂Cl 11-365 Cl F H OCH₂C≡CCH₂Cl 11-366 Cl Cl H OCH₂C≡CCH₂Cl 11-367 H F H OCH₂CN 11-368 H Cl H OCH₂CN 11-369 F F H OCH₂CN 11-370 F Cl H OCH₂CN 1I-371 Cl F H OCH₂CN 11-372 Cl Cl H OCH₂CN 11-373 H F H OCH₂OCH₃ 11-374 H Cl H OCH₂OCH₃ 11-375 F F H OCH₂OCH₃

TABLE 140 X Y R¹ B 11-376 F Cl H OCH₂OCH₃ 11-377 Cl F H OCH₂OCH₃ 11-378 Cl Cl H OCH₂OCH₃ 11-379 H F H OCH₂OC₂H₅ 11-380 H Cl H OCH₂OC₂H₅ 11-381 F F H OCH₂OC₂H₅ 11-382 F Cl H OCH₂OC₂H₅ 11-383 Cl F H OCH₂OC₂H₅ 11-384 Cl Cl H OCH₂OC₂H₅ 11-385 H F H OCH₂SCH₃ 11-386 H Cl H OCH₂SCH₃ 11-387 F F H OCH₂SCH₃ 11-388 F Cl H OCH₂SCH₃ 11-389 Cl F H OCH₂SCH₃ 11-390 Cl Cl H OCH₂SCH₃ 11-391 H F H OCH₂COOH 11-392 H Cl H OCH₂COOH 11-393 F F H OCH₂COOH 11-394 F Cl H OCH₂COOH 11-395 Cl F H OCH₂COOH 11-396 Cl Cl H OCH₂COOH 11-397 H F H OCH₂COOCH₃ 11-398 H Cl H OCH₂COOCH₃ 11-399 F F H OCH₂COOCH₃ 11-400 F Cl H OCH₂COOCH₃

TABLE 141 X Y R¹ B 11-401 Cl F H OCH₂COOCH₃ 11-402 Cl Cl H OCH₂COOCH₃ 11-403 H F H OCH₂COOC₂H₅ 11-404 H Cl H OCH₂COOC₂H₅ 11-405 F F H OCH₂COOC₂H₅ 11-406 F Cl H OCH₂COOC₂H₅ 11-407 Cl F H OCH₂COOC₂H₅ 11-408 Cl Cl H OCH₂COOC₂H₅ 11-409 H F H OCH₂COOnC₃H₇ 11-410 H Cl H OCH₂COOnC₃H₇ 11-411 F F H OCH₂COOnC₃H₇ 11-412 F Cl H OCH₂COOnC₃H₇ 11-413 Cl F H OCH₂COOnC₃H₇ 11-414 Cl Cl H OCH₂COOnC₃H₇ 11-415 H F H OCH₂COOnC₄H₉ 11-416 H Cl H OCH₂COOnC₄H₉ 11-417 F F H OCH₂COOnC₄H₉ 11-418 F Cl H OCH₂COOnC₄H₉ 11-419 Cl F H OCH₂COOnC₄H₉ 11-420 Cl Cl H OCH₂COOnC₄H₉ 11-421 H F H OCH₂COOnC₅H₁₁ 11-422 H Cl H OCH₂COOnC₅H₁₁ 11-423 F F H OCH₂COOnC₅H₁₁ 11-424 F Cl H OCH₂COOnC₅H₁₁ 11-425 Cl F H OCH₂COOnC₅H₁₁

TABLE 142 X Y R¹ B 11-426 Cl Cl H OCH₂COOnC₅H₁₁ 11-427 H F H OCH₂COOiC₃H₇ 11-428 H Cl H OCH₂COOiC₃H₇ 11-429 F F H OCH₂COOiC₃H₇ 11-430 F Cl H OCH₂COOiC₃H₇ 11-431 Cl F H OCH₂COOiC₃H₇ 11-432 Cl Cl H OCH₂COOiC₃H₇ 11-433 H F H OCH₂COOcC₅H₉ 11-434 H Cl H OCH₂COOcC₅H₉ 11-435 F F H OCH₂COOcC₅H₉ 11-436 F Cl H OCH₂COOcC₅H₉ 11-437 Cl F H OCH₂COOcC₅H₉ 11-438 Cl Cl H OCH₂COOcC₅H₉ 11-439 H F H OCH₂COOcC₆H₁₁ 11-440 H Cl H OCH₂COOcC₆H₁₁ 11-441 F F H OCH₂COOcC₆H₁₁ 11-442 F Cl H OCH₂COOcC₆H₁₁ 11-443 Cl F H OCH₂COOcC₆H₁₁ 11-444 Cl Cl H OCH₂COOcC₆H₁₁ 11-445 H F H OCH(CH₃)COOH 11-446 H Cl H OCH(CH₃)COOH 11-447 F F H OCH(CH₃)COOH 11-448 F Cl H OCH(CH₃)COOH 11-449 Cl F H OCH(CH₃)COOH 11-450 Cl Cl H OCH(CH₃)COOH

TABLE 143 X Y R¹ B 11-451 H F H OCH(CH₃)COOCH₃ 11-452 H Cl H OCH(CH₃)COOCH₃ 11-453 F F H OCH(CH₃)COOCH₃ 11-454 F Cl H OCH(CH₃)COOCH₃ 11-455 Cl F H OCH(CH₃)COOCH₃ 11-456 Cl Cl H OCH(CH₃)COOCH₃ 11-457 H F H OCH(CH₃)COOC₂H₅ 11-458 H Cl H OCH(CH₃)COOC₂H₅ 11-459 F F H OCH(CH₃)COOC₂H₅ 11-460 F Cl H OCH(CH₃)COOC₂H₅ 11-461 Cl F H OCH(CH₃)COOC₂H₅ 11-462 Cl Cl H OCH(CH₃)COOC₂H₅ 11-463 H F H OCH(CH₃)COOnC₃H₇ 11-464 H Cl H OCH(CH₃)COOnC₃H₇ 11-465 F F H OCH(CH₃)COOnC₃H₇ 11-466 F Cl H OCH(CH₃)COOnC₃H₇ 11-467 Cl F H OCH(CH₃)COOnC₃H₇ 11-468 Cl Cl H OCH(CH₃)COOnC₃H₇ 11-469 H F H OCH(CH₃)COOnC₄H₉ 11-470 H Cl H OCH(CH₃)COOnC₄H₉ 11-471 F F H OCH(CH₃)COOnC₄H₉ 11-472 F Cl H OCH(CH₃)COOnC₄H₉ 11-473 Cl F H OCH(CH₃)COOnC₄H₉ 11-474 Cl Cl H OCH(CH₃)COOnC₄H₉ 11-475 H F H OCH(CH₃)COOnC₅H₁₁

TABLE 144 X Y R¹ B 11-476 H Cl H OCH(CH₃)COOnC₅H₁₁ 11-477 F F H OCH(CH₃)COOnC₅H₁₁ 11-478 F Cl H OCH(CH₃)COOnC₅H₁₁ 11-479 Cl F H OCH(CH₃)COOnC₅H₁₁ 11-480 Cl Cl H OCH(CH₃)COOnC₅H₁₁ 11-481 H F H OCH(CH₃)COOiC₃H₇ 11-482 H Cl H OCH(CH₃)COOiC₃H₇ 11-483 F F H OCH(CH₃)COOiC₃H₇ 11-484 F Cl H OCH(9H₃)COOiC₃H₇ 11-485 Cl F H OCH(CH₃)COOiC₃H₇ 11-486 Cl Cl H OCH(CH₃)COOiC₃H₇ 11-487 H F H OCH(CH₃)COOcC₅H₉ 11-488 H Cl H OCH(CH₃)COOcC₅H₉ 11-489 F F H OCH(CH₃)COOcC₅H₉ 11-490 F Cl H OCH(CH₃)COOcC₅H₉ 11-491 Cl F H OCH(CH₃)COOcC₅H₉ 11-492 Cl Cl H OCH(CH₃)CGOcC₅H₉ 11-493 H F H OCH(CH₃)COOcC₆H₁₁ 11-494 H Cl H OCH(CH₃)COOcC₆H₁₁ 11-495 F F H OCH(CH₃)COOcC₆H₁₁ 11-496 F Cl H OCH(CH₃)COOcC₆H₁₁ 11-497 Cl F H OCH(CH₃)COOcC₆H₁₁ 11-498 Cl Cl H OCH(CH₃)COOcC₆H₁₁ 11-499 H F H OCH₂CONH₂ 11-500 H Cl H OCH₂CONH₂

TABLE 145 X Y R¹ B 11-501 F F H OCH₂CONH₂ 11-502 F Cl H OCH₂CONH₂ 11-503 Cl F H OCH₂CONH₂ 11-504 Cl Cl H OCH₂CONH₂ 11-505 H F H OCH₂CONHCH₃ 11-506 H Cl H OCH₂CONHCH₃ 11-507 F F H OCH₂CONHCH₃ 11-508 F Cl H OCH₂CONHCH₃ 11-509 Cl F H OCH₂CONHCH₃ 11-510 Cl Cl H OCH₂CONHCH₃ 11-511 H F H OCH₂CON(CH₃)₂ 11-512 H Cl H OCH₂CON(CH₃)₂ 11-513 F F H OCH₂CON(CH₃)₂ 11-514 F Cl H OCH₂CON(CH₃)₂ 11-515 Cl F H OCH₂CON(CH₃)₂ 11-516 Cl Cl H OCH₂CON(CH₃)₂ 11-517 H F H OCH₂CON(C₂H₅)₂ 11-518 H Cl H OCH₂CON(C₂H₅)₂ 11-519 F F H OCH₂CON(C₂H₅)₂ 11-520 F Cl H OCH₂CON(C₂H₅)₂ 11-521 Cl F H OCH₂CON(C₂H₅)₂ 11-522 Cl Cl H OCH₂CON(C₂H₅)₂ 11-523 H F H OCH₂CON(CH₃)C₂H₅ 11-524 H Cl H OCH₂CON(CH₃)C₂H₅ 11-525 F F H OCH₂CON(CH₃)C₂H₅

TABLE 146 X Y R¹ B 11-526 F Cl H OCH₂CON(CH₃)C₂H₅ 11-527 Cl F H OCH₂CON(CH₃)C₂H₅ 11-528 Cl Cl H OCH₂CON(CH₃)C₂H₅ 11-529 H F H OCH₂CON(tetramethylene) 11-530 H Cl H OCH₂CON(tetramethylene) 11-531 F F H OCH₂CON(tetramethylene) 11-532 F C1 H OCH₂CON(tetramethylene) 11-533 Cl F H OCH₂CON(tetramethylene) 11-534 Cl Cl H OCH₂CON(tetramethylene) 11-535 H F H OCH₂CON(pentamethylene) 11-536 H Cl H OCH₂CON(pentamethylene) 11-537 F F H OCH₂CON(pentamethylene) 11-538 F Cl H OCH₂CON(pentamethylene) 11-539 Cl F H OCH₂CON(pentamethylene) 11-540 Cl Cl H OCH₂CON(pentamethylene) 11-541 H F H OCH₂CON(ethyleneoxyethylene) 11-542 H Cl H OCH₂CON(ethyleneoxyethylene) 11-543 F F H OCH₂CON(ethyleneoxyethylene) 11-544 F Cl H OCH₂CON(ethyleneoxyethylene) 11-545 Cl F H OCH₂CON(ethyleneoxyethylene) 11-546 Cl Cl H OCH₂CON(ethyleneoxyethylene) 11-547 H F H OCH(CH₃)CONH₂ 11-548 H Cl H OCH(CH₃)CONH₂ 11-549 F F H OCH(CH₃)CONH₂ 11-550 F Cl H OCH(CH₃)CONH₂

TABLE 147 X Y R¹ B 11-551 Cl F H OCH(CH₃)CONH₂ 11-552 Cl Cl H OCH(CH₃)CONH₂ 11-553 H F H OCH(CH₃)CONHCH₃ 11-554 H Cl H OCH(CH₃)CONHCH₃ 11-555 F F H OCH(CH₃)CONHCH₃ 11-556 F Cl H OCH(CH₃)CONHCH₃ 11-557 Cl F H OCH(CH₃)CONHCH₃ 11-558 Cl Cl H OCH(CH₃)CONHCH₃ 11-559 H F H OCH(CH₃)CON(CH₃)₂ 11-560 H Cl H OCH(CH₃)CON(CH₃)₂ 11-561 F F H OCH(CH₃)CON(CH₃)₂ 11-562 F Cl H OCH(CH₃)CON(CH₃)₂ 11-563 Cl F H OCH(CH₃)CON(CH₃)₂ 11-564 Cl Cl H OCH(CH₃)CON(CH₃)₂ 11-565 H F H OCH(CH₃)CON(C₂H₅)₂ 11-566 H Cl H OCH(CH₃)CON(C₂H₅)₂ 11-567 F F H OCH(CH₃)CON(C₂H₅)₂ 11-568 F Cl H OCH(CH₃)CON(C₂H₅)₂ 11-569 Cl F H OCH(CH₃)CON(C₂H₅)₂ 11-570 Cl Cl H OCH(CH₃)CON(C₂H₅)₂ 11-571 H F H OCH(CH₃)CON(CH₃)C₂H₅ 11-572 H Cl H OCH(CH₃)CON(CH₃)C₂H₅ 11-573 F F H OCH(CH₃)CON(CH₃)C₂H₅ 11-574 F Cl H OCH(CH₃)CON(CH₃)C₂H₅ 11-575 Cl F H OCH(CH₃)CON(CH₃)C₂H₅

TABLE 148 X Y R¹ B 11-576 Cl Cl H OCH(CH₃)CON(CH₃)C₂H₅ 11-577 H F H OCH(CH₃)CON(tetramethylene) 11-578 H Cl H OCH(CH₃)CON(tetramethylene) 11-579 F F H OCH(CH₃)CON(tetramethylene) 11-580 F Cl H OCH(CH₃)CON(tetramethylene) 11-581 Cl F H OCH(CH₃)CON(tetramethylene) 11-582 Cl Cl H OCH(CH₃)CON(tetramethylene) 11-583 H F H OCH(CH₃)CON(pentamethylene) 11-584 H Cl H OCH(CH₃)CON(pentamethylene) 11-585 F F H OCH(CH₃)CON(pentamethylene) 11-586 F Cl H OCH(CH₃)CON(pentamethylene) 11-587 Cl F H OCH(CH₃)CON(pentamethylene) 11-588 Cl Cl H OCH(CH₃)CON(pentamethylene) 11-589 H F H OCH(CH₃)CON(ethyleneoxyethylene) 11-590 H Cl H OCH(CH₃)CON(ethyleneoxyethylene) 11-591 F F H OCH(CH₃)CON(ethyleneoxyethylene) 11-592 F Cl H OCH(CH₃)CON(ethyleneoxyethylene) 11-593 Cl F H OCH(CH₃)CON(ethyleneoxyethylene) 11-594 Cl Cl H OCH(CH₃)CON(ethyleneoxyethylene) 11-595 H F H OCH₂COON(CH₃)₂ 11-596 H Cl H OCH₂COON(CH₃)₂ 11-597 F F H OCH₂COON(CH₃)₂ 11-598 F Cl H OCH₂COON(CH₃)₂ 11-599 Cl F H OCH₂COON(CH₃)₂ 11-600 Cl Cl H OCH₂COON(CH₃)₂

TABLE 149 X Y R¹ B 11-601 H F H OCH₂COON(C₂H₅)₂ 11-602 H Cl H OCH₂COON(C₂H₅)₂ 11-603 F F H OCH₂COON(C₂H₅)₂ 11-604 F Cl H OCH₂COON(C₂H₅)₂ 11-605 Cl F H OCH₂COON(C₂H₅)₂ 11-606 Cl Cl H OCH₂COON(C₂H₅)₂ 11-607 H F H OCH(CH₃)COON(CH₃)₂ 11-608 H Cl H OCH(CH₃)COON(CH₃)₂ 11-609 F F H OCH(CH₃)COON(CH₃)₂ 11-610 F Cl H OCH(CH₃)COON(CH₃)₂ 11-611 Cl F H OCH(CH₃)COON(CH₃)₂ 11-612 Cl Cl H OCH(CH₃)COON(CH₃)₂ 11-613 H F H OCH(CH₃)COON(C₂H₅)₂ 11-614 H Cl H OCH(CH₃)COON(C₂H₅)₂ 11-615 F F H OCH(CH₃)COON(C₂H₅)₂ 11-616 F Cl H OCH(CH₃)COON(C₂H₅)₂ 11-617 Cl F H OCH(CH₃)COON(C₂H₅)₂ 11-618 Cl Cl H OCH(CH₃)COON(C₂H₅)₂ 11-619 H F H SCH₃ 11-620 H Cl H SCH₃ 11-621 F F H SCH₃ 11-622 F Cl H SCH₃ 11-623 Cl F H SCH₃ 11-624 Cl Cl H SCH₃ 11-625 H F H SC₂H₅

TABLE 150 X Y R¹ B 11-626 H Cl H SC₂H₅ 11-627 F F H SC₂H₅ 11-628 F Cl H SC₂H₅ 11-629 Cl F H SC₂H₅ 11-630 Cl Cl H SC₂H₅ 11-631 H F H SiC₃H₇ 11-632 H Cl H SiC₃H₇ 11-633 F F H SiC₃H₇ 11-634 F Cl H SiC₃H₇ 11-635 Cl F H SiC₃H₇ 11-636 Cl Cl H SiC₃H₇ 11-637 H F H SnC₃H₇ 11-638 H Cl H SnC₃H₇ 11-639 F F H SnC₃H₇ 11-640 F Cl H SnC₃H₇ 11-641 Cl F H SnC₃H₇ 11-642 Cl Cl H SnC₃H₇ 11-643 H F H SCH₂CH₂Cl 11-644 H Cl H SCH₂CH₂Cl 11-645 F F H SCH₂CH₂Cl 11-646 F Cl H SCH₂CH₂Cl 11-647 Cl F H SCH₂CH₂Cl 11-648 Cl Cl H SCH₂CH₂Cl 11-649 H F H ScC₅H₉ 11-650 H Cl H ScC₅H₉

TABLE 151 X Y R¹ B 11-651 F F H ScC₅H₉ 11-652 F Cl H ScC₅H₉ 11-653 Cl F H ScC₅H₉ 11-654 Cl Cl H ScC₅H₉ 11-655 H F H ScC₆H₁₁ 11-656 H Cl H ScC₆H₁₁ 11-657 F F H ScC₆H₁₁ 11-658 F Cl H ScC₆H₁₁ 11-659 Cl F H ScC₆H₁₁ 11-660 Cl Cl H ScC₆H₁₁ 11-661 H F H SCH₂CH═CH₂ 11-662 H Cl H SCH₂CH═CH₂ 11-663 F F H SCH₂CH═CH₂ 11-664 F Cl H SCH₂CH═CH₂ 11-665 Cl F H SCH₂CH═CH₂ 11-666 Cl Cl H SCH₂CH═CH₂ 11-667 H F H SCH₂CCl═CH₂ 11-668 H Cl H SCH₂CCl═CH₂ 11-669 F F H SCH₂CCl═CH₂ 11-670 F Cl H SCH₂CCl═CH₂ 11-671 Cl F H SCH₂CCl═CH₂ 11-672 Cl Cl H SCH₂CCl═CH₂ 11-673 H F H SCH₂CCl═CHCl 11-674 H Cl H SCH₂CCl═CHCl 11-675 F F H SCH₂CCl═CHCl

TABLE 152 X Y R¹ B 11-676 F Cl H SCH₂CCl═CHCl 11-677 Cl F H SCH₂CCl═CHCl 11-678 Cl Cl H SCH₂CCl═CHCl 11-679 H F H SCH(CH₃)CH═CH₂ 11-680 H Cl H SCH(CH₃)CH═CH₂ 11-681 F F H SCH(CH₃)CH═CH₂ 11-682 F Cl H SCH(CH₃)CH═CH₂ 11-683 Cl F H SCH(CH₃)CH═CH₂ 11-684 Cl Cl H SCH(CH₃)CH═CH₂ 11-685 H F H SCH₂C≡CH 11-686 H Cl H SCH₂C≡CH 11-687 F F H SCH₂C≡CH 11-688 F Cl H SCH₂C≡CH 11-689 Cl F H SCH₂C≡CH 11-690 Cl Cl H SCH₂C≡CH 11-691 H F H SCH(CH₃)C≡CH 11-692 H Cl H SCH(CH₃)C≡CH 11-693 F F H SCH(CH₃)C≡CH 11-694 F Cl H SCH(CH₃)C≡CH 11-695 Cl F H SCH(CH₃)C≡CH 11-696 Cl Cl H SCH(CH₃)C≡CH 11-697 H F H SCH₂COOH 11-698 H Cl H SCH₂COOH 11-699 F F H SCH₂COOH 11-700 F Cl H SCH₂COOH

TABLE 153 X Y R¹ B 11-701 Cl F H SCH₂COOH 11-702 Cl Cl H SCH₂COOH 11-703 H F H SCH₂COOCH₃ 11-704 H Cl H SCH₂COOCH₃ 11-705 F F H SCH₂COOCH₃ 11-706 F Cl H SCH₂COOCH₃ 11-707 Cl F H SCH₂COOCH₃ 11-708 Cl Cl H SCH₂COOCH₃ 11-709 H F H SCH₂COOC₂H₅ 11-710 H Cl H SCH₂COOC₂H₅ 11-711 F F H SCH₂COOC₂H₅ 11-712 F Cl H SCH₂COOC₂H₅ 11-713 Cl F H SCH₂COOC₂H₅ 11-714 Cl Cl H SCH₂COOC₂H₅ 11-715 H F H SCH₂COOnC₃H₇ 11-716 H Cl H SCH₂COOnC₃H₇ 11-717 F F H SCH₂COOnC₃H₇ 11-718 F Cl H SCH₂COOnC₃H₇ 11-719 Cl F H SCH₂COOnC₃H₇ 11-720 Cl Cl H SCH₂COOnC₃H₇ 11-721 H F H SCH₂COOnC₄H₉ 11-722 H Cl H SCH₂COOnC₄H₉ 11-723 F F H SCH₂COOnC₄H₉ 11-724 F Cl H SCH₂COOnC₄H₉ 11-725 Cl F H SCH₂COOnC₄H₉

TABLE 154 X Y R¹ B 11-726 Cl Cl H SCH₂COOnC₄H₉ 11-727 H F H SCH₂COOnC₅H₁₁ 11-728 H Cl H SCH₂COOnC₅H₁₁ 11-729 F F H SCH₂COOnC₅H₁₁ 11-730 F Cl H SCH₂COOnC₅H₁₁ 11-731 Cl F H SCH₂COOnC₅H₁₁ 11-732 Cl Cl H SCH₂COOnC₅H₁₁ 11-733 H F H SCH₂COOiC₃H₇ 11-734 H Cl H SCH₂COOiC₃H₇ 11-735 F F H SCH₂COOiC₃H₇ 11-736 F Cl H SCH₂COOiC₃H₇ 11-737 Cl F H SCH₂COOiC₃H₇ 11-738 Cl Cl H SCH₂COOiC₃H₇ 11-739 H F H SCH₂COOCC₅H₉ 11-740 H Cl H SCH₂COOCC₅H₉ 11-741 F F H SCH₂COOCC₅H₉ 11-742 F Cl H SCH₂CQOcC₅H₉ 11-743 Cl F H SCH₂COOcC₅H₉ 11-744 Cl Cl H SCH₂COOCC₅H₉ 11-745 H F H SCH₂COOCC₆H₁₁ 11-746 H Cl H SCH₂COOCC₆H₁₁ 11-747 F F H SCH₂COOcC₆H₁₁ 11-748 F Cl H SCH₂COOcC₆H₁₁ 11-749 Cl F H SCH₂COOeC₆H₁₁ 11-750 Cl Cl H SCH₂COOcC₆H₁₁

TABLE 155 X Y R¹ B 11-751 H F H SCH(CH₃)COOH 11-752 H Cl H SCH(CH₃)COOH 11-753 F F H SCH(CH₃)COOH 11-754 F Cl H SCH(CH₃)COOH 11-755 Cl F H SCH(CH₃)COOH 11-756 Cl Cl H SCH(CH₃)COOH 11-757 H F H SCH(CH₃)COOCH₃ 11-758 H Cl H SCH(CH₃)COOCH₃ 11-759 F F H SCH(CH₃)COOCH₃ 11-760 F Cl H SCH(CH₃)COOCH₃ 11-761 Cl F H SCH(CH₃)COOCH₃ 11-762 Cl Cl H SCH(CH₃)COOCH₃ 11-763 H F H SCH(CH₃)COOC₂H₅ 11-764 H Cl H SCH(CH₃)COOC₂H₅ 11-765 F F H SCH(CH₃)COOC₂H₅ 11-766 F Cl H SCH(CH₃)COOC₂H₅ 11-767 Cl F H SCH(CH₃)COOC₂H₅ 11-768 Cl Cl H SCH(CH₃)COOC₂H₅ 11-769 H F H SCH(CH₃)COOnC₃H₇ 11-770 H Cl H SCH(CH₃)COOnC₃H₇ 11-771 F F H SCH(CH₃)COOnC₃H₇ 11-772 F Cl H SCH(CH₃)COOnC₃H₇ 11-773 Cl F H SCH(CH₃)COOnC₃H₇ 11-774 Cl Cl H SCH(CH₃)COOnC₃H₇ 11-775 H F H SCH(CH₃)COOnC₄H₉

TABLE 156 X Y R¹ B 11-776 H Cl H SCH(CH₃)COOnC₄H₉ 11-777 F F H SCH(CH₃)COOnC₄H₉ 11-778 F Cl H SCH(CH₃)COOnC₄H₉ 11-779 Cl F H SCH(CH₃)COOnC₄H₉ 11-780 Cl Cl H SCH(CH₃)COOnC₄H₉ 11-781 H F H SCH(CH₃)COOnC₅H₁₁ 11-782 H Cl H SCH(CH₃)COOnC₅H₁₁ 11-783 F F H SCH(CH₃)COOnC₅H₁₁ 11-784 F Cl H SCH(CH₃)COOnC₅H₁₁ 11-785 Cl F H SCH(CH₃)COOnC₅H₁₁ 11-786 Cl Cl H SCH(CH₃)COOnC₅H₁₁ 11-787 H F H SCH(CH₃)COOiC₃H₇ 11-788 H Cl H SCH(CH₃)COOiC₃H₇ 11-789 F F H SCH(CH₃)COOiC₃H₇ 11-790 F Cl H SCH(CH₃)COOiC₃H₇ 11-791 Cl F H SCH(CH₃)COOiC₃H₇ 11-792 Cl Cl H SCH(CH₃)COOiC₃H₇ 11-793 H F H SCH(CH₃)COOcC₅H₉ 11-794 H Cl H SCH(CH₃)COOcC₅H₉ 11-795 F F H SCH(CH₃)COOcC₅H₉ 11-796 F Cl H SCH(CH₃)COOcC₅H₉ 11-797 Cl F H SCH(CH₃)COOcC₅H₉ 11-798 Cl Cl H SCH(CH₃)COOcC₅H₉ 11-799 H F H SCH(CH₃)COOcC₆H₁₁ 11-800 H Cl H SCH(CH₃)COOcC₆H₁₁

TABLE 157 X Y R¹ B 11-801 F F H SCH(CH₃)COOcC₆H₁₁ 11-802 F Cl H SCH(CH₃)COOcC₆H₁₁ 11-803 Cl F H SCH(CH₃)COOcC₆H₁₁ 11-804 Cl Cl H SCH(CH₃)COOcC₆H₁₁ 11-805 H F H SCH₂CONH₂ 11-806 H Cl H SCH₂CONH₂ 11-807 F F H SCH₂CONH₂ 11-808 F Cl H SCH₂CONH₂ 11-809 Cl F H SCH₂CONH₂ 11-810 Cl Cl H SCH₂CONH₂ 11-811 H F H SCH₂CONHCH₃ 11-812 H Cl H SCH₂CONHCH₃ 11-813 F F H SCH₂CONHCH₃ 11-814 F Cl H SCH₂CONHCH₃ 11-815 Cl F H SCH₂CONHCH₃ 11-816 Cl Cl H SCH₂CONHCH₃ 11-817 H F H SCH₂CON(CH₃)₂ 11-818 H Cl H SCH₂CON(CH₃)₂ 11-819 F F H SCH₂CON(CH₃)₂ 11-820 F Cl H SCH₂CON(CH₃)₂ 11-821 Cl F H SCH₂CON(CH₃)₂ 11-822 Cl Cl H SCH₂CON(CH₃)₂ 11-823 H F H SCH₂CON(C₂H₅)₂ 11-824 H Cl H SCH₂CON(C₂H₅)₂ 11-825 F F H SCH₂CON(C₂H₅)₂

TABLE 158 X Y R¹ B 11-826 F Cl H SCH₂CON(C₂H₅)₂ 11-827 Cl F H SCH₂CON(C₂H₅)₂ 11-828 Cl Cl H SCH₂CON(C₂H₅)₂ 11-829 H F H SCH₂CON(CH₃)C₂H₅ 11-830 H Cl H SCH₂CON(CH₃)C₂H₅ 11-831 F F H SCH₂CON(CH₃)C₂H₅ 11-832 F Cl H SCH₂CON(CH₃)C₂H₅ 11-833 Cl F H SCH₂CON(CH₃)C₂H₅ 11-834 Cl Cl H SCH₂CON(CH₃)C₂H₅ 11-835 H F H SCH₂CON(tetramethylene) 11-836 H Cl H SCH₂CON(tetramethylene) 11-837 F F H SCH₂CON(tetramethylene) 11-838 F Cl H SCH₂CON(tetramethylene) 11-839 Cl F H SCH₂CON(tetramethylene) 11-840 Cl Cl H SCH₂CON(tetramethylene) 11-841 H F H SCH₂CON(pentamethylene) 11-842 H Cl H SCH₂CON(pentamethylene) 11-843 F F H SCH₂CON(pentamethylene) 11-844 F Cl H SCH₂CON(pentamethylene) 11-845 Cl F H SCH₂CON(pentamethylene) 11-846 Cl Cl H SCH₂CON(pentamethylene) 11-847 H F H SCH₂CON(ethyleneoxyethylene) 11-848 H Cl H SCH₂CON(ethyleneoxyethylene) 11-849 F F H SCH₂CON(ethyleneoxyethylene) 11-850 F Cl H SCH₂CON(ethyleneoxyethylene)

TABLE 159 X Y R¹ B 11-851 Cl F H SCH₂CON(ethyleneoxyethylene) 11-852 Cl Cl H SCH₂CON(ethyleneoxyethylene) 11-853 H F H SCH(CH₃)CONH₂ 11-854 H Cl H SCH(CH₃)CONH₂ 11-855 F F H SCH(CH₃)CONH₂ 11-856 F Cl H SCH(CH₃)CONH₂ 11-857 Cl F H SCH(CH₃)CONH₂ 11-858 Cl Cl H SCH(CH₃)CONH₂ 11-859 H F H SCH(CH₃)CONHCH₃ 11-860 H Cl H SCH(CH₃)CONHCH₃ 11-861 F F H SCH(CH₃)CONHCH₃ 11-862 F Cl H SCH(CH₃)CONHCH₃ 11-863 Cl F H SCH(CH₃)CONHCH₃ 11-864 Cl Cl H SCH(CH₃)CONHCH₃ 11-865 H F H SCH(CH₃)CON(CH₃)₂ 11-866 H Cl H SCH(CH₃)CON(CH₃)₂ 11-867 F F H SCH(CH₃)CON(CH₃)₂ 11-868 F Cl H SCH(CH₃)CON(CH₃)₂ 11-869 Cl F H SCH(CH₃)CON(CH₃)₂ 11-870 Cl Cl H SCH(CH₃)CON(CH₃)₂ 11-871 H F H SCH(CH₃)CON(C₂H₅)₂ 11-872 H Cl H SCH(CH₃)CON(C₂H₅)₂ 11-873 F F H SCH(CH₃)CON(C₂H₅)₂ 11-874 F Cl H SCH(CH₃)CON(C₂H₅)₂ 11-875 Cl F H SCH(CH₃)CON(C₂H₅)₂

TABLE 160 X Y R¹ B 11-876 Cl Cl H SCH(CH₃)CON(C₂H₅)₂ 11-877 H F H SCH(CH₃)CON(CH₃)C₂H₅ 11-878 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 11-879 F F H SCH(CH₃)CON(CH₃)C₂H₅ 11-880 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 11-881 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 11-882 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 11-883 H F H SCH(CH₃)CON(CH₃)C₂H₅ 11-884 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 11-885 F F H SCH(CH₃)CON(CH₃)C₂H₅ 11-886 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 11-887 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 11-888 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 11-889 H F H SCH(CH₃)CON(tetramethylene) 11-890 H Cl H SCH(CH₃)CON(tetramethylene) 11-891 F F H SCH(CH₃)CON(tetramethylene) 11-892 F Cl H SCH(CH₃)CON(tetramethylene) 11-893 Cl F H SCH(CH₃)CON(tetramethylene) 11-894 Cl Cl H SCH(CH₃)CON(tetramethylene) 11-895 H F H SCH(CH₃)CON(pentamethylene) 11-896 H Cl H SCH(CH₃)CON(pentamethylene) 11-897 F F H SCH(CH₃)CON(pentamethylene) 11-898 F Cl H SCH(CH₃)CON(pentamethylene) 11-899 Cl F H SCH(CH₃)CON(pentamethylene) 11-900 Cl Cl H SCH(CH₃)CON(pentamethylene)

TABLE 161 X Y R¹ B 11-901 H F H SCH(CH₃)CON(ethyleneoxyethylene) 11-902 H Cl H SCH(CH₃)CON(ethyleneoxyethylene) 11-903 F F H SCH(CH₃)CON(ethyleneoxyethylene) 11-904 F Cl H SCH(CH₃)CON(ethyleneoxyethylene) 11-905 Cl F H SCH(CH₃)CON(ethyleneoxyethylene) 11-906 Cl Cl H SCH(CH₃)CON(ethyleneoxyethylene) 11-907 H F H SO₂OCH₃ 11-908 H Cl H SO₂OCH₃ 11-909 F F H SO₂OCH₃ 11-910 F Cl H SO₂OCH₃ 11-911 Cl F H SO₂OCH₃ 11-912 Cl Cl H SO₂OCH₃ 11-913 H F H SO₂OC₂H₅ 11-914 H Cl H SO₂OC₂H₅ 11-915 F F H SO₂OC₂H₅ 11-916 F Cl H SO₂OC₂H₅ 11-917 Cl F H SO₂OC₂H₅ 11-918 Cl Cl H SO₂OC₂H₅ 11-919 H F H SO₂OiC₃H₇ 11-920 H Cl H SO₂OiC₃H₇ 11-921 F F H SO₂OiC₃H₇ 11-922 F Cl H SO₂OiC₃H₇ 11-923 Cl F H SO₂OiC₃H₇ 11-924 Cl Cl H SO₂OiC₃H₇ 11-925 H F H SO₂OCH₂CH═CH₂

TABLE 162 X Y R¹ B 11-926 H Cl H SO₂OCH₂CH═CH₂ 11-927 F F H SO₂OCH₂CH═CH₂ 11-928 F Cl H SO₂OCH₂CH═CH₂ 11-929 Cl F H SO₂OCH₂CH═CH₂ 11-930 Cl Cl H SO₂OCH₂CH═CH₂ 11-931 H F H SO₂N(CH₃)₂ 11-932 H Cl H SO₂N(CH₃)₂ 11-933 F F H SO₂N(CH₃)₂ 11-934 F Cl H SO₂N(CH₃)₂ 11-935 Cl F H SO₂N(CH₃)₂ 11-936 Cl Cl H SO₂N(CH₃)₂ 11-937 H F H SO₂N(C₂H₅)₂ 11-938 H Cl H SO₂N(C₂H₅)₂ 11-939 F F H SO₂N(C₂H₅)₂ 11-940 F Cl H SO₂N(C₂H₅)₂ 11-941 Cl F H SO₂N(C₂H₅)₂ 11-942 Cl Cl H SO₂N(C₂H₅)₂ 11-943 H F H COOH 11-944 H Cl H COOH 11-945 F F H COOH 11-946 F Cl H COOH 11-947 Cl F H COOH 11-948 Cl Cl H COOH 11-949 H F H COOCH₃ 11-950 H Cl H COOCH₃

TABLE 163 X Y R¹ B 11-951 F F H COOCH₃ 11-952 F Cl H COOCH₃ 11-953 Cl F H COOCH₃ 11-954 Cl Cl H COOCH₃ 11-955 H F H COOC₂H₅ 11-956 H Cl H COOC₂H₅ 11-957 F F H COOC₂H₅ 11-958 F Cl H COOC₂H₅ 11-959 Cl F H COOC₂H₅ 11-960 Cl Cl H COOC₂H₅ 11-961 H F H COOnC₃H₇ 11-962 H Cl H COOnC₃H₇ 11-963 F F H COOnC₃H₇ 11-964 F Cl H COOnC₃H₇ 11-965 Cl F H COOnC₃H₇ 11-966 Cl Cl H COOnC₃H₇ 11-967 H F H COOnC₄H₉ 11-968 H Cl H COOnC₄H₉ 11-969 F F H COOnC₄H₉ 11-970 F Cl H COOnC₄H₉ 11-971 Cl F H COOnC₄H₉ 11-972 Cl Cl H COOnC₄H₉ 11-973 H F H COOnC₅H₁₁ 11-974 H Cl H COOnC₅H₁₁ 11-975 F F H COOnC₅H₁₁

TABLE 164 X Y R¹ B 11-976 F Cl H COOnC₅H₁₁ 11-977 Cl F H COOnC₅H₁₁ 11-978 Cl Cl H COOnC₅H₁₁ 11-979 H F H COOiC₃H₇ 11-980 H Cl H COOiC₃H₇ 11-981 F F H COOiC₃H₇ 11-982 F Cl H COOiC₃H₇ 11-983 Cl F H COOiC₃H₇ 11-984 Cl Cl H COOiC₃H₇ 11-985 H F H COOcC₅H₉ 11-986 H Cl H COOcC₅H₉ 11-987 F F H COOcC₅H₉ 11-988 F Cl H COOcC₅H₉ 11-989 Cl F H COOcC₅H₉ 11-990 Cl Cl H COOcC₅H₉ 11-991 H F H COOcC₆H₁₁ 11-992 H Cl H COOcC₆H₁₁ 11-993 F F H COOcC₆H₁₁ 11-994 F Cl H COOcC₆H₁₁ 11-995 Cl F H COOcC₆H₁₁ 11-996 Cl Cl H COOcC₆H₁₁ 11-997 H F H COOCH₂C₆H₅ 11-998 H Cl H COOCH₂C₆H₅ 11-999 F F H COOCH₂C₆H₅  11-1000 F Cl H COOCH₂C₆H₅

TABLE 165 X Y R¹ B 11-1001 Cl F H COOCH₂C₆H₅ 11-1002 Cl Cl H COOCH₂C₆6H₅ 11-1003 H F H COOCH₂CH₂Cl 11-1004 H Cl H COOCH₂CH₂Cl 11-1005 F F H COOCH₂CH₂Cl 11-1006 F Cl H COOCH₂CH₂Cl 11-1007 Cl F H COOCH₂CH₂Cl 11-1008 Cl Cl H COOCH₂CH₂Cl 11-1009 H F H COOCH₂CH₂Br 11-1010 H Cl H COOCH₂CH₂Br 11-1011 F F H COOCH₂CH₂Br 11-1012 F Cl H COOCH₂CH₂Br 11-1013 Cl F H COOCH₂CH₂Br 11-1014 Cl Cl H COOCH₂CH₂Br 11-1015 H F H CONH₂ 11-1016 H Cl H CONH₂ 11-1017 F F H CONH₂ 11-1018 F Cl H CONH₂ 11-1019 Cl F H CONH₂ 11-1020 Cl Cl H CONH₂ 11-1021 H F H CONHCH₃ 11-1022 H Cl H CONHCH₃ 11-1023 F F H CONHCH₃ 11-1024 F Cl H CONHCH₃ 11-1025 Cl F H CONHCH₃

TABLE 166 X Y R¹ B 11-1026 Cl Cl H CONHCH₃ 11-1027 H F H CONHC₂H₅ 11-1028 H Cl H CONHC₂H₅ 11-1029 F F H CONHC₂H₅ 11-1030 F Cl H CONHC₂H₅ 11-1031 Cl F H CONHC₂H₅ 11-1032 Cl Cl H CONHC₂H₅ 11-1033 H F H CON(CH₃)₂ 11-1034 H Cl H CON(CH₃)₂ 11-1035 F F H CON(CH₃)₂ 11-1036 F Cl H CON(CH₃)₂ 11-1037 Cl F H CON(CH₃)₂ 11-1038 Cl Cl H CON(CH₃)₂ 11-1039 H F H CON(C₂H₅)₂ 11-1040 H Cl H CON(C₂H₅)₂ 11-1041 F F H CON(C₂H₅)₂ 11-1042 F Cl H CON(C₂H₅)₂ 11-1043 Cl F H CON(C₂H₅)₂ 11-1044 Cl Cl H CON(C₂H₅)₂ 11-1045 H F H CON(CH₃)(C₂H₅) 11-1046 H Cl H CON(CH₃)(C₂H₅) 11-1047 F F H CON(CH₃)(C₂H₅) 11-1048 F Cl H CON(CH₃)(C₂H₅) 11-1049 Cl F H CON(CH₃)(C₂H₅) 11-1050 Cl Cl H CON(CH₃)(C₂H₅)

TABLE 167 X Y R¹ B 11-1051 H F H COCH₃ 11-1052 H Cl H COCH₃ 11-1053 F F H COCH₃ 11-1054 F Cl H COCH₃ 11-1055 Cl F H COCH₃ 11-1056 Cl Cl H COCH₃ 11-1057 H F H COC₂H₅ 11-1058 H Cl H COC₂H₅ 11-1059 F F H COC₂H₅ 11-1060 F Cl H COC₂H₅ 11-1061 Cl F H COC₂H₅ 11-1062 Cl Cl H COC₂H₅ 11-1063 H F H COCH₂Cl 11-1064 H Cl H COCH₂Cl 11-1065 F F H COCH₂Cl 11-1066 F Cl H COCH₂Cl 11-1067 Cl F H COCH₂Cl 11-1068 Cl Cl H COCH₂Cl 11-1069 H F H CHO 11-1070 H Cl H CHO 11-1071 F F H CHO 11-1072 F Cl H CHO 11-1073 Cl F H CHO 11-1074 Cl Cl H CHO 11-1075 H F H CH₂CH₂COOH

TABLE 168 X Y R¹ B 11-1076 H Cl H CH₂CH₂COOH 11-1077 F F H CH₂CH₂COOH 11-1078 F Cl H CH₂CH₂COOH 11-1079 Cl F H CH₂CH₂COOH 11-1080 Cl Cl H CH₂CH₂COOH 11-1081 H F H CH₂CH₂COOCH₃ 11-1082 H Cl H CH₂CH₂COOCH₃ 11-1083 F F H CH₂CH₂COOCH₃ 11-1084 F Cl H CH₂CH₂COOCH₃ 11-1085 Cl F H CH₂CH₂COOCH₃ 11-1086 Cl Cl H CH₂CH₂COOCH₃ 11-1087 H F H CH₂CH₂COOC₂H₅ 11-1088 H Cl H CH₂CH₂COOC₂H₅ 11-1089 F F H CH₂CH₂COOC₂H₅ 11-1090 F Cl H CH₂CH₂COOC₂H₅ 11-1091 Cl F H CH₂CH₂COOC₂H₅ 11-1092 Cl Cl H CH₂CH₂COOC₂H₅ 11-1093 H F H CH₂CHClCOOCH₃ 11-1094 H Cl H CH₂CHClCOOCH₃ 11-1095 F F H CH₂CHClCOOCH₃ 11-1096 F Cl H CH₂CHClCOOCH₃ 11-1097 Cl F H CH₂CHClCOOCH₃ 11-1098 Cl Cl H CH₂CHClCOOCH₃ 11-1099 H F H CH₂CHClCOOC₂H₅ 11-1100 H Cl H CH₂CHClCOOC₂H₅

TABLE 169 X Y R¹ B 11-1101 F F H CH₂CHClCOOC₂H₅ 11-1102 F Cl H CH₂CHClCOOC₂H₅ 11-1103 Cl F H CH₂CHClCOOC₂H₅ 11-1104 Cl Cl H CH₂CHClCOOC₂H₅ 11-1105 H F H CH═CHCOOCH₃ 11-1106 H Cl H CH═CHCOOCH₃ 11-1107 F F H CH═CHCOOCH₃ 11-1108 F Cl H CH═CHCOOCH₃ 11-1109 Cl F H CH═CHCOOCH₃ 11-1110 Cl Cl H CH═CHCOOCH₃ 11-1111 H F H CH═CHCOOC₂H₅ 11-1112 H Cl H CH═CHCOOC₂H₅ 11-1113 F F H CH═CHCOOC₂H₅ 11-1114 F Cl H CH═CHCOOC₂H₅ 11-1115 Cl F H CH═CHCOOC₂H₅ 11-1116 Cl Cl H CH═CHCOOC₂H₅ 11-1117 H F H C(CH₃)═NOH 11-1118 H Cl H C(CH₃)═NOH 11-1119 F F H C(CH₃)═NOH 11-1120 F Cl H C(CH₃)═NOH 11-1121 Cl F H C(CH₃)═NOH 11-1122 Cl Cl H C(CH₃)═NOH 11-1123 H F H C(CH₃)═NOCH₃ 11-1124 H Cl H C(CH₃)═NOCH₃ 11-1125 F F H C(CH₃)═NOCH₃

TABLE 170 X Y R¹ B 11-1126 F Cl H C(CH₃)═NOCH₃ 11-1127 Cl F H C(CH₃)═NOCH₃ 11-1128 Cl Cl H C(CH₃)═NOCH₃ 11-1129 H F H C(CH₃)═NOC₂H₅ 11-1130 H Cl H C(CH₃)═NOC₂H₅ 11-1131 F F H C(CH₃)═NOC₂H₅ 11-1132 F Cl H C(CH₃)═NOC₂H₅ 11-1133 Cl F H C(CH₃)═NOC₂H₅ 11-1134 Cl Cl H C(CH₃)═NOC₂H₅ 11-1135 H F H C(CH₃)═NOiC₃H₇ 11-1136 H Cl H C(CH₃)═NOiC₃H₇ 11-1137 F F H C(CH₃)═NOiC₃H₇ 11-1138 F Cl H C(CH₃)═NOiC₃H₇ 11-1139 Cl F H C(CH₃)═NOiC₃H₇ 11-1140 Cl Cl H C(CH₃)═NOiC₃H₇ 11-1141 H F H C(CH₃)═NNH₂ 11-1142 H Cl H C(CH₃)═NNH₂ 11-1143 F F H C(CH₃)═NNH₂ 11-1144 F Cl H C(CH₃)═NNH₂ 11-1145 Cl F H C(CH₃)═NNH₂ 11-1146 Cl Cl H C(CH₃)═NNH₂ 11-1147 H F H C(CH₃)═NNHCH₃ 11-1148 H Cl H C(CH₃)═NNHCH₃ 11-1149 F F H C(CH₃)═NNHCH₃ 11-1150 F Cl H C(CH₃)═NNHCH₃

TABLE 171 X Y R¹ B 11-1151 Cl F H C(CH₃)═NNHCH₃ 11-1152 Cl Cl H C(CH₃)═NNHCH₃ 11-1153 H F H C(CH₃)═NN(CH₃)₂ 11-1154 H Cl H C(CH₃)═NN(CH₃)₂ 11-1155 F F H C(CH₃)═NN(CH₃)₂ 11-1156 F Cl H C(CH₃)═NN(CH₃)₂ 11-1157 Cl F H C(CH₃)═NN(CH₃)₂ 11-1158 Cl Cl H C(CH₃)═NN(CH₃)₂ 11-1159 H F H C(CH₃)═NNHC₂H₅ 11-1160 H Cl H C(CH₃)═NNHC₂H₅ 11-1161 F F H C(CH₃)═NNHC₂H₅ 11-1162 F Cl H C(CH₃)═NNHC₂H₅ 11-1163 Cl F H C(CH₃)═NNHC₂H₅ 11-1164 Cl Cl H C(CH₃)═NNHC₂H₅ 11-1165 H F H C(CH₃)═NN(C₂H₅)₂ 11-1166 H Cl H C(CH₃)═NN(C₂H₅)₂ 11-1167 F F H C(CH₃)═NN(C₂H₅)₂ 11-1168 F Cl H C(CH₃)═NN(C₂H₅)₂ 11-1169 Cl F H C(CH₃)═NN(C₂H₅)₂ 11-1170 Cl Cl H C(CH₃)═NN(C₂H₅)₂ 11-1171 H F H C(C₂H₅)═NNH₂ 11-1172 H Cl H C(C₂H₅)═NNH₂ 11-1173 F F H C(C₂H₅)═NNH₂ 11-1174 F Cl H C(C₂H₅)═NNH₂ 11-1175 Cl F H C(C₂H₅)═NNH₂

TABLE 172 X Y R¹ B 11-1176 Cl Cl H C(C₂H₅)═NNH₂ 11-1177 H F H C(C₂H₅)═NNHCH₃ 11-1178 H Cl H C(C₂H₅)═NNHCH₃ 11-1179 F F H C(C₂H₅)═NNHCH₃ 11-1180 F Cl H C(C₂H₅)═NNHCH₃ 11-1181 Cl F H C(C₂H₅)═NNHCH₃ 11-1182 Cl Cl H C(C₂H₅)═NNHCH₃ 11-1183 H F H C(C₂H₅)═NN(CH₃)₂ 11-1184 H Cl H C(C₂H₅)═NN(CH₃)₂ 11-1185 F F H C(C₂H₅)═NN(CH₃)₂ 11-1186 F Cl H C(C₂H₅)═NN(CH₃)₂ 11-1187 Cl F H C(C₂H₅)═NN(CH₃)₂ 11-1188 Cl Cl H C(C₂H₅)═NN(CH₃)₂ 11-1189 H F H C(C₂H₅)═NNHC₂H₅ 11-1190 H Cl H C(C₂H₅)═NNHC₂H₅ 11-1191 F F H C(C₂H₅)═NNHC₂H₅ 11-1192 F Cl H C(C₂H₅)═NNHC₂H₅ 11-1193 Cl F H C(C₂H₅)═NNHC₂H₅ 11-1194 Cl Cl H C(C₂H₅)═NNHC₂H₅ 11-1195 H F H C(C₂H₅)═NN(C₂H₅)₂ 11-1196 H Cl H C(C₂H₅)═NN(C₂H₅)₂ 11-1197 F F H C(C₂H₅)═NN(C₂H₅)₂ 11-1198 F Cl H C(C₂H₅)═NN(C₂H₅)₂ 11-1199 Cl F H C(C₂H₅)═NN(C₂H₅)₂ 11-1200 Cl Cl H C(C₂H₅)═NN(C₂H₅)₂

TABLE 173 X Y R¹ B 11-1201 H F H C(CH₃)(OCH₃)₂ 11-1202 H Cl H C(CH₃)(OCH₃)₂ 11-1203 F F H C(CH₃)(OCH₃)₂ 11-1204 F Cl H C(CH₃)(OCH₃)₂ 11-1205 Cl F H C(CH₃)(OCH₃)₂ 11-1206 Cl Cl H C(CH₃)(OCH₃)₂ 11-1207 H F H C(CH₃)(OC₂H₅)₂ 11-1208 H Cl H C(CH₃)(OC₂H₅)₂ 11-1209 F F H C(CH₃)(OC₂H₅)₂ 11-1210 F Cl H C(CH₃)(OC₂H₅)₂ 11-1211 Cl F H C(CH₃)(OC₂H₅)₂ 11-1212 Cl Cl H C(CH₃)(OC₂H₅)₂ 11-1213 H F H C(CH₃)(OiC₃H₇)₂ 11-1214 H Cl H C(CH₃)(OiC₃H₇)₂ 11-1215 F F H C(CH₃)(OiC₃H₇)₂ 11-1216 F Cl H C(CH₃)(OiC₃H₇)₂ 11-1217 Cl F H C(CH₃)(OiC₃H₇)₂ 11-1218 Cl Cl H C(CH₃)(OiC₃H₇)₂ 11-1219 H F H C(CH₃)(OCH₂CH₂O) 11-1220 H Cl H C(CH₃)(OCH₂CH₂O) 11-1221 F F H C(CH₃)(OCH₂CH₂O) 11-1222 F Cl H C(CH₃)(OCH₂CH₂O) 11-1223 Cl F H C(CH₃)(OCH₂CH₂O) 11-1224 Cl Cl H C(CH₃)(OCH₂CH₂O) 11-1225 H F H C(CH₃)(OCH₂CH₂CH₂O)

TABLE 174 X Y R¹ B 11-1226 H Cl H C(CH₃)(OCH₂CH₂CH₂O) 11-1227 F F H C(CH₃)(OCH₂CH₂CH₂O) 11-1228 F Cl H C(CH₃)(OCH₂CH₂CH₂O) 11-1229 Cl F H C(CH₃)(OCH₂CH₂CH₂O) 11-1230 Cl Cl H C(CH₃)(OCH₂CH₂CH₂O) 11-1231 H F H C(C₂H₅)(OCH₂CH₂O) 11-1232 H Cl H C(C₂H₅)(OCH₂CH₂O) 11-1233 F F H C(C₂H₅)(OCH₂CH₂O) 11-1234 F Cl H C(C₂H₅)(OCH₂CH₂O) 11-1235 Cl F H C(C₂H₅)(OCH₂CH₂O) 11-1236 Cl Cl H C(C₂H₅)(OCH₂CH₂O) 11-1237 H F H C(C₂H₅)(OCH₂CH₂CH₂O) 11-1238 H Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 11-1239 F F H C(C₂H₅)(OCH₂CH₂CH₂O) 11-1240 F Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 11-1241 Cl F H C(C₂H₅)(OCH₂CH₂CH₂O) 11-1242 Cl Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 11-1243 H F H OCH₂CH(CH₃)₂ 11-1244 H Cl H OCH₂CH(CH₃)₂ 11-1245 F F H OCH₂CH(CH₃)₂ 11-1246 F Cl H OCH₂CH(CH₃)₂ 11-1247 Cl F H OCH₂CH(CH₃)₂ 11-1248 Cl Cl H OCH₂CH(CH₃)₂ 11-1249 H F H OCH₂CH₂F 11-1250 H Cl H OCH₂CH₂F

TABLE 175 X Y R¹ B 11-1251 F F H OCH₂CH₂F 11-1252 F Cl H OCH₂CH₂F 11-1253 Cl F H OCH₂CH₂F 11-1254 Cl Cl H OCH₂CH₂F 11-1255 H Cl H CH₂OH 11-1256 F Cl H CH₂OH 11-1257 H Cl H CH₂OCOCH₃ 11-1258 F Cl H CH₂OCOCH₃

Compounds of the general formula:

TABLE 176 X Z¹ n R¹ R⁴ R⁵ 12-1  H O 1 H H H 12-2  F O 1 H H H 12-3  H O 1 H H CH₃ 12-4  F O 1 H H CH₃ 12-5  H O 1 H H C₂H₅ 12-6  F O 1 H H C₂H₅ 12-7  H O 1 H H nC₃H₇ 12-8  F O 1 H H nC₃H₇ 12-9  H O 1 H H nC₄H₉ 12-10 F O 1 H H nC₄H₉ 12-11 H O 1 H H nC₅H₁₁ 12-12 F O 1 H H nC₅H₁₁ 12-13 H O 1 H H iC₃H₇ 12-14 F O 1 H H iC₃H₇ 12-15 H O 1 H H CH₂CH₂Cl 12-16 F O 1 H H CH₂CH₂Cl 12-17 H O 1 H H CH₂CH₂Br 12-18 F O 1 H H CH₂CH₂Br 12-19 H O 1 H H CH₂CH═CH₂ 12-20 F O 1 H H CH₂CH═CH₂ 12-21 H O 1 H H CH(CH₃)CH═CH₂ 12-22 F O 1 H H CH(CH₃)CH═CH₂ 12-23 H O 1 H H CH₂CCl═CH₂ 12-24 F O 1 H H CH₂CCl═CH₂ 12-25 H O 1 H H CH₂C≡CH

TABLE 177 X Z¹ n R¹ R⁴ R⁵ 12-26 F O 1 H H CH₂C≡CH 12-27 H O 1 H H CH(CH₃)C≡CH 12-28 F O 1 H H CH(CH₃)C≡CH 12-29 H O 1 H H CH₂CN 12-30 F O 1 H H CH₂CN 12-31 H O 1 H H CH₂OCH₃ 12-32 F O 1 H H CH₂OCH₃ 12-33 H O 1 H H CH₂OC₂H₅ 12-34 F O 1 H H CH₂OC₂H₅ 12-35 H O 1 H H CH₂COOH 12-36 F O 1 H H CH₂COOH 12-37 H O 1 H H CH₂COOCH₃ 12-38 F O 1 H H CH₂COOCH₃ 12-39 H O 1 H H CH₂COOC₂H₅ 12-40 F O 1 H H CH₂COOC₂H₅ 12-41 H O 1 H H CH₂COOnC₃H₇ 12-42 F O 1 H H CH₂COOnC₃H₇ 12-43 H O 1 H H CH₂COOnC₄H₉ 12-44 F O 1 H H CH₂COOnC₄H₉ 12-45 H O 1 H H CH₂COOnC₅H₁₁ 12-46 F O 1 H H CH₂COOnC₅H₁₁ 12-47 H O 1 H H CH₂COOiC₃H₇ 12-48 F O 1 H H CH₂COOiC₃H₇ 12-49 H O 1 H H CH₂COOcC₅H₉ 12-50 F O 1 H H CH₂COOcC₅H₉

TABLE 178 X Z¹ n R¹ R⁴ R⁵ 12-51 H O 1 H H CH₂COOcC₆H₁₁ 12-52 F O 1 H H CH₂COOcC₆H₁₁ 12-53 H O 1 H H CH(CH₃)COOH 12-54 F O 1 H H CH(CH₃)COOH 12-55 H O 1 H H CH(CH₃)COOCH₃ 12-56 F O 1 H H CH(CH₃)COOCH₃ 12-57 H O 1 H H CH(CH₃)COOC₂H₅ 12-58 F O 1 H H CH(CH₃)COOC₂H₅ 12-59 H O 1 H H CH(CH₃)COOnC₃H₇ 12-60 F O 1 H H CH(CH₃)COOnC₃H₇ 12-61 H O 1 H H CH(CH₃)COOnC₄H₉ 12-62 F O 1 H H CH(CH₃)COOnC₄H₉ 12-63 H O 1 H H CH(CH₃)COOnC₅H₁₁ 12-64 F O 1 H H CH(CH₃)COOnC₅H₁₁ 12-65 H O 1 H H CH(CH₃)COOiC₃H₇ 12-66 F O 1 H H CH(CH₃)COOiC₃H₇ 12-67 H O 1 H H CH(CH₃)COOcC₅H₉ 12-68 F O 1 H H CH(CH₃)COOcC₅H₉ 12-69 H O 1 H H CH(CH₃)COOcC₆H₁₁ 12-70 F O 1 H H CH(CH₃)COOcC₆H₁₁ 12-71 H O 1 H CH₃ H 12-72 F O 1 H CH₃ H 12-73 H O 1 H CH₃ CH₃ 12-74 F O 1 H CH₃ CH₃ 12-75 H O 1 H CH₃ C₂H₅

TABLE 179 X Z¹ n R¹ R⁴ R⁵ 12-76 F O 1 H CH₃ C₂H₅ 12-77 H O 1 H CH₃ nC₃H₇ 12-78 F O 1 H CH₃ nC₃H₇ 12-79 H O 1 H CH₃ nC₄H₉ 12-80 F O 1 H CH₃ nC₄H₉ 12-81 H O 1 H CH₃ nC₅H₁₁ 12-82 F O 1 H CH₃ nC₅H₁₁ 12-83 H O 1 H CH₃ iC₃H₇ 12-84 F O 1 H CH₃ iC₃H₇ 12-85 H O 1 H CH₃ CH₂CH₂Cl 12-86 F O 1 H CH₃ CH₂CH₂Cl 12-87 H O 1 H CH₃ CH₂CH₂Br 12-88 F O 1 H CH₃ CH₂CH₂Br 12-89 H O 1 H CH₃ CH₂CH═CH₂ 12-90 F O 1 H CH₃ CH₂CH═CH₂ 12-91 H O 1 H CH₃ CH(CH₃)CH═CH₂ 12-92 F O 1 H CH₃ CH(CH₃)CH═CH₂ 12-93 H O 1 H CH₃ CH₂CCl═CH₂ 12-94 F O 1 H CH₃ CH₂CCl═CH₂ 12-95 H O 1 H CH₃ CH₂C≡CH 12-96 F O 1 H CH₃ CH₂C≡CH 12-97 H O 1 H CH₃ CH(CH₃)C≡CH 12-98 F O 1 H CH₃ CH(CH₃)C≡CH 12-99 H O 1 H CH₃ CH₂CN  12-100 F O 1 H CH₃ CH₂CN

TABLE 180 X Z¹ n R¹ R⁴ R⁵ 12-101 H O 1 H CH₃ CH₂OCH₃ 12-102 F O 1 H CH₃ CH₂OCH₃ 12-103 H O 1 H CH₃ CH₂OC₂H₅ 12-104 F O 1 H CH₃ CH₂OC₂H₅ 12-105 H O 0 H — H 12-106 F O 0 H — H 12-107 H O 0 H — CH₃ 12-108 F O 0 H — CH₃ 12-109 H O 0 H — C₂H₅ 12-110 F O 0 H — C₂H₅ 12-111 H O 0 H — nC₃H₇ 12-112 F O 0 H — nC₃H₇ 12-113 H O 0 H — nC₄H₉ 12-114 F O 0 H — nC₄H₉ 12-115 H O 0 H — nC₅H₁₁ 12-116 F O 0 H — nC₅H₁₁ 12-117 H O 0 H — iC₃H₇ 12-118 F O 0 H — iC₃H₇ 12-119 H O 0 H — CH₂CH₂Cl 12-120 F O 0 H — CH₂CH₂Cl 12-121 H O 0 H — CH₂CH₂Br 12-122 F O 0 H — CH₂CH₂Br 12-123 H O 0 H — CH₂CH═CH₂ 12-124 F O 0 H — CH₂CH═CH₂ 12-125 H O 0 H — CH(CH₃)CH═CH₂

TABLE 181 X Z¹ n R¹ R⁴ R⁵ 12-126 F O 0 H — CH(CH₃)CH═CH₂ 12-127 H O 0 H — CH₂CCl═CH₂ 12-128 F O 0 H — CH₂CCl═CH₂ 12-129 H O 0 H — CH₂C≡CH 12-130 F O 0 H — CH₂C≡CH 12-131 H O 0 H — CH(CH₃)C≡CH 12-132 F O 0 H — CH(CH₃)C≡CH 12-133 H O 0 H — CH₂CN 12-134 F O 0 H — CH₂CN 12-135 H O 0 H — CH₂OCH₃ 12-136 F O 0 H — CH₂OCH₃ 12-137 H O 0 H — CH₂OC₂H₅ 12-138 F O 0 H — CH₂OC₂H₅ 12-139 H S 0 H — H 12-140 F S 0 H — H 12-141 H S 0 H — CH₃ 12-142 F S 0 H — CH₃ 12-143 H S 0 H — C₂H₅ 12-144 F S 0 H — C₂H₅ 12-145 H S 0 H — nC₃H₇ 12-146 F S 0 H — nC₃H₇ 12-147 H S 0 H — nC₄H₉ 12-148 F S 0 H — nC₄H₉ 12-149 H S 0 H — nC₅H₁₁ 12-150 F S 0 H — nC₅H₁₁

TABLE 182 X Z¹ n R¹ R⁴ R⁵ 12-151 H S 0 H — iC₃H₇ 12-152 F S 0 H — iC₃H₇ 12-153 H S 0 H — CH₂CH₂Cl 12-154 F S 0 H — CH₂CH₂Cl 12-155 H S 0 H — CH₂CH₂Br 12-156 F S 0 H — CH₂CH₂Br 12-157 H S 0 H — CH₂CH═CH₂ 12-158 F S 0 H — CH₂CH═CH₂ 12-159 H S 0 H — CH(CH₃)CH═CH₂ 12-160 F S 0 H — CH(CH₃)CH═CH₂ 12-161 H S 0 H — CH₂CCl═CH₂ 12-162 F S 0 H — CH₂CCl═CH₂ 12-163 H S 0 H — CH₂C≡CH 12-164 F S 0 H — CH₂C≡CH 12-165 H S 0 H — CH(CH₃)C≡CH 12-166 F S 0 H — CH(CH₃)C≡CH 12-167 H S 0 H — CH₂CN 12-168 F S 0 H — CH₂CN 12-169 H S 0 H — CH₂OCH₃ 12-170 F S 0 H — CH₂OCH₃ 12-171 H S 0 H — CH₂OC₂H₅ 12-172 F S 0 H — CH₂OC₂H₅ 12-173 H S 0 H — CH₂COOH 12-174 F S 0 H — CH₂COOH 12-175 H S 0 H — CH₂COOCH₃

TABLE 183 X Z¹ n R¹ R⁴ R⁵ 12-176 F S 0 H — CH₂COOCH₃ 12-177 H S 0 H — CH₂COOC₂H₅ 12-178 F S 0 H — CH₂COOC₂H₅ 12-179 H S 0 H — CH₂COOnC₃H₇ 12-180 F S 0 H — CH₂COOnC₃H₇ 12-181 H S 0 H — CH₂COOnC₄H₉ 12-182 F S 0 H — CH₂COOnC₄H₉ 12-183 H S 0 H — CH₂COOnC₅H₁₁ 12-184 F S 0 H — CH₂COOnC₅H₁₁ 12-185 H S 0 H — CH₂COOiC₃H₇ 12-186 F S 0 H — CH₂COOiC₃H₇ 12-187 H S 0 H — CH₂COOcC₅H₉ 12-188 F S 0 H — CH₂COOcC₅H₉ 12-189 H S 0 H — CH₂COOcC₆H₁₁ 12-190 F S 0 H — CH₂COOcC₆H₁₁ 12-191 H S 0 H — CH(CH₃)COOH 12-192 F S 0 H — CH(CH₃)COOH 12-193 H S 0 H — CH(CH₃)COOCH₃ 12-194 F S 0 H — CH(CH₃)COOCH₃ 12-195 H S 0 H — CH(CH₃)COOC₂H₅ 12-196 F S 0 H — CH(CH₃)COOC₂H₅ 12-197 H S 0 H — CH(CH₃)COOnC₃H₇ 12-198 F S 0 H — CH(CH₃)COOnC₃H₇ 12-199 H S 0 H — CH(CH₃)COOnC₄H₉ 12-200 F S 0 H — CH(CH₃)COOnC₄H₉

TABLE 184 X Z¹ n R¹ R⁴ R⁵ 12-201 H S 0 H — CH(CH₃)COOnC₅H₁₁ 12-202 F S 0 H — CH(CH₃)COOnC₅H₁₁ 12-203 H S 0 H — CH(CH₃)COOiC₃H₇ 12-204 F S 0 H — CH(CH₃)COOiC₃H₇ 12-205 H S 0 H — CH(CH₃)COOcC₅H₉ 12-206 F S 0 H — CH(CH₃)COOcC₅H₉ 12-207 H S 0 H — CH(CH₃)COOcC₆H₁₁ 12-208 F S 0 H — CH(CH₃)COOcC₆H₁₁

Compounds of the general formula:

TABLE 185 X R¹ R⁵ 15-1  H H CH₃ 15-2  F H CH₃ 15-3  Cl H CH₃ 15-4  H H C₂H₅ 15-5  F H C₂H₅ 15-6  Cl H C₂H₅ 15-7  H H nC₃H₇ 15-8  F H nC₃H₇ 15-9  Cl H nC₃H₇ 15-10 H H nC₄H₉ 15-11 F H nC₄H₉ 15-12 Cl H nC₄H₉ 15-13 H H iC₄H₉ 15-14 F H iC₄H₉ 15-15 Cl H iC₄H₉ 15-16 H H CH₂CH═CH₂ 15-17 F H CH₂CH═CH₂ 15-18 Cl H CH₂CH═CH₂ 15-19 H H CH(CH₃)CH═CH₂ 15-20 F H CH(CH₃)CH═CH₂ 15-21 Cl H CH(CH₃)CH═CH₂ 15-22 H H CH₂C≡CH 15-23 F H CH₂C≡CH 15-24 Cl H CH₂C≡CH 15-25 H H CH(CH₃)C≡CH

TABLE 186 X R¹ R⁵ 15-26 F H CH(CH₃)CH≡CH 15-27 Cl H CH(CH₃)CH≡CH

Compounds of the general formula:

TABLE 187 X Y R¹ B 16-1  H F H H 16-2  H Cl H H 16-3  H Br H H 16-4  F F H H 16-5  F Cl H H 16-6  F Br H H 16-7  Cl F H H 16-8  Cl Cl H H 16-9  Cl Br H H 16-10 H F H NO₂ 16-11 H Cl H NO₂ 16-12 H Br H NO₂ 16-13 F F H NO₂ 16-14 F Cl H NO₂ 16-15 F Br H NO₂ 16-16 Cl F H NO₂ 16-17 Cl Cl H NO₂ 16-18 Cl Br H NO₂ 16-19 H F H NH₂ 16-20 H Cl H NH₂ 16-21 H Br H NH₂ 16-22 F F H NH₂ 16-23 F Cl H NH₂ 16-24 F Br H NH₂ 16-25 Cl F H NH₂

TABLE 188 X Y R¹ B 16-26 Cl Cl H NH₂ 16-27 Cl Br H NH₂ 16-28 H F H OH 16-29 H Cl H OH 16-30 H Br H OH 16-31 F F H OH 16-32 F Cl H OH 16-33 F Br H OH 16-34 Cl F H OH 16-35 Cl Cl H OH 16-36 Cl Br H OH 16-37 H F H SH 16-38 H Cl H SH 16-39 H Br H SH 16-40 F F H SH 16-41 F Cl H SH 16-42 F Br H SH 16-43 Cl F H SH 16-44 Cl Cl H SH 16-45 Cl Br H SH 16-46 H F H SO₂Cl 16-47 H Cl H SO₂Cl 16-48 H Br H SO₂Cl 16-49 F F H SO₂Cl 16-50 F Cl H SO₂Cl

TABLE 189 X Y R¹ B 16-51 F Br H SO₂Cl 16-52 Cl F H SO₂Cl 16-53 Cl Cl H SO₂Cl 16-54 Cl Br H SO₂Cl 16-55 H F H NHCH₃ 16-56 H Cl H NHCH₃ 16-57 F F H NHCH₃ 16-58 F Cl H NHCH₃ 16-59 Cl F H NHCH₃ 16-60 Cl Cl H NHCH₃ 16-61 H F H NHC₂H₅ 16-62 H Cl H NHC₂H₅ 16-63 F F H NHC₂H₅ 16-64 F C1 H NHC₂H₅ 16-65 Cl F H NHC₂H₅ 16-66 Cl Cl H NHC₂H₅ 16-67 H F H NHCH₂CH═CH₂ 16-68 H Cl H NHCH₂CH═CH₂ 16-69 F F H NHCH₂CH═CH₂ 16-70 F Cl H NHCH₂CH═CH₂ 16-71 Cl F H NHCH₂CH═CH₂ 16-72 Cl Cl H NHCH₂CH═CH₂ 16-73 H F H NHCH₂C≡CH 16-74 H Cl H NHCH₂C≡CH 16-75 F F H NHCH₂C≡CH

TABLE 190 X Y R¹ B 16-76 F Cl H NHCH₂C≡CH 16-77 Cl F H NHCH₂C≡CH 16-78 Cl Cl H NHCH₂C≡CH 16-79 H F H NHCH(CH₃)C≡CH 16-80 H Cl H NHCH(CH₃)C≡CH 16-81 F F H NHCH(CH₃)C≡CH 16-82 F Cl H NHCH(CH₃)C≡CH 16-83 Cl F H NHCH(CH₃)C≡CH 16-84 Cl Cl H NHCH(CH₃)C≡CH 16-85 H F H NHSO₂CH₃ 16-86 H Cl H NHSO₂CH₃ 16-87 F F H NHSO₂CH₃ 16-88 F Cl H NHSO₂CH₃ 16-89 Cl F H NHSO₂CH₃ 16-90 Cl CL H NHSO₂CH₃ 16-91 H F H NHSO₂C₂H₅ 16-92 H Cl H NHSO₂C₂H₅ 16-93 F F H NHSO₂C₂H₅ 16-94 F Cl H NHSO₂C₂H₅ 16-95 Cl F H NHSO₂C₂H₅ 16-96 Cl Cl H NHSO₂C₂H₅ 16-97 H F H NHSO₂CH₂Cl 16-98 H Cl H NHSO₂CH₂Cl 16-99 F F H NHSO₂CH₂Cl  16-100 F Cl H NHSO₂CH₂Cl

TABLE 191 X Y R¹ B 16-101 Cl F H NHSO₂CH₂Cl 16-102 Cl Cl H NHSO₂CH₂Cl 16-103 H F H NHSO₂CF₃ 16-104 H Cl H NHSO₂CF₃ 16-105 F F H NHSO₂CF₃ 16-106 F Cl H NHSO₂CF₃ 16-107 Cl F H NHSO₂CF₃ 16-108 Cl Cl H NHSO₂CF₃ 16-109 H F H N(SO₂CH₃)₂ 16-110 H Cl H N(SO₂CH₃)₂ 16-111 F F H N(SO₂CH₃)₂ 16-112 F Cl H N(SO₂CH₃)₂ 16-113 Cl F H N(SO₂CH₃)₂ 16-114 Cl Cl H N(SO₂CH₃)₂ 16-115 H F H N(CH₃)SO₂CH₃ 16-116 H Cl H N(CH₃)SO₂CH₃ 16-117 F F H N(CH₃)SO₂CH₃ 16-118 F Cl H N(CH₃)SO₂CH₃ 16-119 Cl F H N(CH₃)SO₂CH₃ 16-120 Cl Cl H N(CH₃)SO₂CH₃ 16-121 H F H N(CH₂C≡CH)SO₂CH₃ 16-122 H Cl H N(CH₂C≡CH)SO₂CH₃ 16-123 F F H N(CH₂C≡CH)SO₂CH₃ 16-124 F Cl H N(CH₂C≡CH)SO₂CH₃ 16-125 Cl F H N(CH₂C≡CH)SO₂CH₃

TABLE 192 X Y R¹ B 16-126 Cl Cl H N(CH₂C≡CH)SO₂CH₃ 16-127 H F H NHCOOCH₃ 16-128 H Cl H NHCOOCH₃ 16-129 F F H NHCOOCH₃ 16-130 F Cl H NHCOOCH₃ 16-131 Cl F H NHCOOCH₃ 16-132 Cl Cl H NHCOOCH₃ 16-133 H F H NHCOOC₂H₅ 16-134 H Cl H NHCOOC₂H₅ 16-135 F F H NHCOOC₂H₅ 16-136 F Cl H NHCOOC₂H₅ 16-137 Cl F H NHCOOC₂H₅ 16-138 Cl Cl H NHCOOC₂H₅ 16-139 H F H NHCOOnC₃H₇ 16-140 H Cl H NHCOOnC₃H₇ 16-141 F F H NHCOOnC₃H₇ 16-142 F Cl H NHCOOnC₃H₇ 16-143 Cl F H NHCOOnC₃H₇ 16-144 Cl Cl H NHCOOnC₃H₇ 16-145 H F H NHCOOiC₃H₇ 16-146 H Cl H NHCOOiC₃H₇ 16-147 F F H NHCOOiC₃H₇ 16-148 F Cl H NHCOOiC₃H₇ 16-149 Cl F H NHCOOiC₃H₇ 16-150 Cl Cl H NHCOOiC₃H₇

TABLE 193 X Y R¹ B 16-151 H F H NHCOOnC₄H₉ 16-152 H Cl H NHCOOnC₄H₉ 16-153 F F H NHCOOnC₄H₉ 16-154 F Cl H NHCOOnC₄H₉ 16-155 Cl F H NHCOOnC₄H₉ 16-156 Cl Cl H NHCOOnC₄H₉ 16-157 H F H NHCOOnC₅H₁₁ 16-158 H Cl H NHCOOnC₅H₁₁ 16-159 F F H NHCOOnC₅H₁₁ 16-160 F Cl H NHCOOnC₅H₁₁ 16-161 Cl F H NHCOOnC₅H₁₁ 16-162 Cl Cl H NHCOOnC₅H₁₁ 16-163 H F H NHCH₂COOCH₃ 16-164 H Cl H NHCH₂COOCH₃ 16-165 F F H NHCH₂COOCH₃ 16-166 F Cl H NHCH₂COOCH₃ 16-167 Cl F H NHCH₂COOCH₃ 16-168 Cl Cl H NHCH₂COOCH₃ 16-169 H F H NHCH₂COOC₂H₅ 16-170 H Cl H NHCH₂COOC₂H₅ 16-171 F F H NHCH₂COOC₂H₅ 16-172 F Cl H NHCH₂COOC₂H₅ 16-173 Cl F H NHCH₂COOC₂H₅ 16-174 Cl Cl H NHCH₂COOC₂H₅ 16-175 H F H NHCH₂COOnC₃H₇

TABLE 194 X Y R¹ B 16-176 H Cl H NHCH₂COOnC₃H₇ 16-177 F F H NHCH₂COOnC₃H₇ 16-178 F Cl H NHCH₂COOnC₃H₇ 16-179 Cl F H NHCH₂COOnC₃H₇ 16-180 Cl Cl H NHCH₂COOnC₃H₇ 16-181 H F H NHCH₂COOnC₄H₉ 16-182 H Cl H NHCH₂COOnC₄H₉ 16-183 F F H NHCH₂COOnC₄H₉ 16-184 F Cl H NHCH₂COOnC₄H₉ 16-185 Cl F H NHCH₂COOnC₄H₉ 16-186 Cl Cl H NHCH₂COOnC₄H₉ 16-187 H F H NHCH₂COOnC₅H₁₁ 16-188 H Cl H NHCH₂COOnC₅H₁₁ 16-189 F F H NHCH₂COOnC₅H₁₁ 16-190 F Cl H NHCH₂COOnC₅H₁₁ 16-191 Cl F H NHCH₂COOnC₅H₁₁ 16-192 Cl Cl H NHCH₂COOnC₅H₁₁ 16-193 H F H NHCH₂COOiC₃H₇ 16-194 H Cl H NHCH₂COOiC₃H₇ 16-195 F F H NHCH₂COOiC₃H₇ 16-196 F Cl H NHCH₂COOiC₃H₇ 16-197 Cl F H NHCH₂COOiC₃H₇ 16-198 Cl Cl H NHCH₂COOiC₃H₇ 16-199 H F H NHCH₂COOcC₅H₉ 16-200 H Cl H NHCH₂COOcC₅H₉

TABLE 195 X Y R¹ B 16-201 F F H NHCH₂COOcC₅H₉ 16-202 F Cl H NHCH₂COOcC₅H₉ 16-203 Cl F H NHCH₂COOcC₅H₉ 16-204 Cl Cl H NHCH₂COOcC₅H₉ 16-205 H F H NHCH₂COOcC₆H₁₁ 16-206 H Cl H NHCH₂COOcC₆H₁₁ 16-207 F F H NHCH₂COOcC₆H₁₁ 16-208 F Cl H NHCH₂COOcC₆H₁₁ 16-209 Cl F H NHCH₂COOcC₆H₁₁ 16-210 Cl Cl H NHCH₂COOcC₆H₁₁ 16-211 H F H NHCH(CH₃)COOCH₃ 16-212 H Cl H NHCH(CH₃)COOCH₃ 16-213 F F H NHCH(CH₃)COOCH₃ 16-214 F Cl H NHCH(CH₃)COOCH₃ 16-215 Cl F H NHCH(CH₃)COOCH₃ 16-216 Cl Cl H NHCH(CH₃)COOCH₃ 16-217 H F H NHCH(CH₃)COOC₂H₅ 16-218 H Cl H NHCH(CH₃)COOC₂H₅ 16-219 F F H NHCH(CH₃)COOC₂H₅ 16-220 F Cl H NHCH(CH₃)COOC₂H₅ 16-221 Cl F H NHCH(CH₃)COOC₂H₅ 16-222 Cl Cl H NHCH(CH₃)COOC₂H₅ 16-223 H F H NHCH(CH₃)COOnC₃H₇ 16-224 H Cl H NHCH(CH₃)COOnC₃H₇ 16-225 F F H NHCH(CH₃)COOnC₃H₇

TABLE 196 X Y R¹ B 16-226 F Cl H NHCH(CH₃)COOnC₃H₇ 16-227 Cl F H NHCH(CH₃)COOnC₃H₇ 16-228 Cl Cl H NHCH(CH₃)COOnC₃H₇ 16-229 H F H NHCH(CH₃)COOnC₄H₉ 16-230 H Cl H NHCH(CH₃)COOnC₄H₉ 16-231 F F H NHCH(CH₃)COOnC₄H₉ 16-232 F Cl H NHCH(CH₃)COOnC₄H₉ 16-233 Cl F H NHCH(CH₃)COOnC₄H₉ 16-234 Cl Cl H NHCH(CH₃)COOnC₄H₉ 16-235 H F H NHCH(CH₃)COOnC₅H₁₁ 16-236 H Cl H NHCH(CH₃)COOnC₅H₁₁ 16-237 F F H NHCH(CH₃)COOnC₅H₁₁ 16-238 F Cl H NHCH(CH₃)COOnC₅H₁₁ 16-239 Cl F H NHCH(CH₃)COOnC₅H₁₁ 16-240 Cl Cl H NHCH(CH₃)COOnC₅H₁₁ 16-241 H F H NHCH(CH₃)COOiC₃H₇ 16-242 H Cl H NHCH(CH₃)COOiC₃H₇ 16-243 F F H NHCH(CH₃)COOiC₃H₇ 16-244 F Cl H NHCH(CH₃)COOiC₃H₇ 16-245 Cl F H NHCH(CH₃)COOiC₃H₇ 16-246 Cl Cl H NHCH(CH₃)COOiC₃H₇ 16-247 H F H NHCH(CH₃)COOcC₅H₉ 16-248 H Cl H NHCH(CH₃)COOcC₅H₉ 16-249 F F H NHCH(CH₃)COOcC₅H₉ 16-250 F Cl H NHCH(CH₃)COOcC₅H₉

TABLE 197 X Y R¹ B 16-251 Cl F H NHCH(CH₃)COOcC₅H₉ 16-252 Cl Cl H NHCH(CH₃)COOcC₅H₉ 16-253 H F H NHCH(CH₃)COOcC₆H₁₁ 16-254 H Cl H NHCH(CH₃)COOcC₆H₁₁ 16-255 F F H NHCH(CH₃)COOcC₆H₁₁ 16-256 F Cl H NHCH(CH₃)COOcC₆H₁₁ 16-257 Cl F H NHCH(CH₃)COOcC₆H₁₁ 16-258 Cl Cl H NHCH(CH₃)COOcC₆H₁₁ 16-259 H F H OCH₃ 16-260 H Cl H OCH₃ 16-261 F F H OCH₃ 16-262 F Cl H OCH₃ 16-263 Cl F H OCH₃ 16-264 Cl Cl H OCH₃ 16-265 H F H OC₂H₅ 16-266 H Cl H OC₂H₅ 16-267 F F H OC₂H₅ 16-268 F Cl H OC₂H₅ 16-269 Cl F H OC₂H₅ 16-270 Cl Cl H OC₂H₅ 16-271 H F H OiC₃H₇ 16-272 H Cl H OiC₃H₇ 16-273 F F H OiC₃H₇ 16-274 F Cl H OiC₃H₇ 16-275 Cl F H OiC₃H₇

TABLE 198 X Y R¹ B 16-276 Cl Cl H OiC₃H₇ 16-277 H F H OnC₃H₇ 16-278 H Cl H OnC₃H₇ 16-279 F F H OnC₃H₇ 16-280 F Cl H OnC₃H₇ 16-281 Cl F H OnC₃H₇ 16-282 Cl CI H OnC₃H₇ 16-283 H F H OCH₂CH₂Cl 16-284 H Cl H OCH₂CH₂Cl 16-285 F F H OCH₂CH₂Cl 16-286 F Cl H OCH₂CH₂Cl 16-287 Cl F H OCH₂CH₂Cl 16-288 Cl Cl H OCH₂CH₂Cl 16-289 H F H OCF₂CF₂H 16-290 H Cl H OCF₂CF₂H 16-291 F F H OCF₂CF₂H 16-292 F Cl H OCF₂CF₂H 16-293 Cl F H OCF₂CF₂H 16-294 Cl Cl H OCF₂CF₂H 16-295 H F H OcC₅H₉ 16-296 H Cl H OcC₅H₉ 16-297 F F H OcC₅H₉ 16-298 F Cl H OcC₅H₉ 16-299 Cl F H OcC₅H₉ 16-300 Cl Cl H OcC₅H₉

TABLE 199 X Y R¹ B 16-301 H F H OcC₆H₁₁ 16-302 H Cl H OcC₆H₁₁ 16-303 F F H OcC₆H₁₁ 16-304 F Cl H OcC₆H₁₁ 16-305 Cl F H OcC₆H₁₁ 16-306 Cl Cl H OcC₆H₁₁ 16-307 H F H OCH₂CH═CH₂ 16-308 H Cl H OCH₂CH═CH₂ 16-309 F F H OCH₂CH═CH₂ 16-310 F Cl H OCH₂CH═CH₂ 16-311 Cl F H OCH₂CH═CH₂ 16-312 Cl Cl H OCH₂CH═CH₂ 16-313 H F H OCH₂CCl═CH₂ 16-314 H Cl H OCH₂CCl═CH₂ 16-315 F F H OCH₂CCl═CH₂ 16-316 F Cl H OCH₂CCl═CH₂ 16-317 Cl F H OCH₂CCl═CH₂ 16-318 Cl Cl H OCH₂CCl═CH₂ 16-319 H F H OCH₂CCl═CHCl 16-320 H Cl H OCH₂CCl═CHCl 16-321 F F H OCH₂CCl═CHCl 16-322 F Cl H OCH₂CCl═CHCl 16-323 Cl F H OCH₂CCl═CHCl 16-324 Cl Cl H OCH₂CCl═CHCl 16-325 H F H OCH(CH₃)CH═CH₂

TABLE 200 X Y R¹ B 16-326 H Cl H OCH(CH₃)CH═CH₂ 16-327 F F H OCH(CH₃)CH═CH₂ 16-328 F Cl H OCH(CH₃)CH═CH₂ 16-329 Cl F H OCH(CH₃)CH═CH₂ 16-330 Cl Cl H OCH(CH₃)CH═CH₂ 16-331 H F H OCH₂C(CH₃)═CH₂ 16-332 H Cl H OCH₂C(CH₃)═CH₂ 16-333 F F H OCH₂C(CH₃)═CH₂ 16-334 F Cl H OCH₂C(CH₃)═CH₂ 16-335 Cl F H OCH₂C(CH₃)═CH₂ 16-336 Cl Cl H OCH₂C(CH₃)═CH₂ 16-337 H F H OCH₂C≡CH 16-338 H Cl H OCH₂C≡CH 16-339 F F H OCH₂C≡CH 16-340 F Cl H OCH₂C≡CH 16-341 Cl F H OCH₂C≡CH 16-342 Cl Cl H OCH₂C≡CH 16-343 H F H OCH(CH₃)C≡CH 16-344 H Cl H OCH(CH₃)C≡CH 16-345 F F H OCH(CH₃)C≡CH 16-346 F Cl H OCH(CH₃)C≡CH 16-347 Cl F H OCH(CH₃)C≡CH 16-348 Cl Cl H OCH(CH₃)C≡CH 16-349 H F H OCH₂C≡CBr 16-350 H Cl H OCH₂C≡CBr

TABLE 201 X Y R¹ B 16-351 F F H OCH₂C≡CBr 16-352 F Cl H OCH₂C≡CBr 16-353 Cl F H OCH₂C≡CBr 16-354 Cl Cl H OCH₂C≡CBr 16-355 H F H OCH₂C≡CCl 16-356 H Cl H OCH₂C≡CCl 16-357 F F H OCH₂C≡CCl 16-358 F Cl H OCH₂C≡CCl 16-359 Cl F H OCH₂C≡CCl 16-360 Cl Cl H OCH₂C≡CCl 16-361 H F H OCH₂C≡CCH₂Cl 16-362 H CI H OCH₂C≡CCH₂Cl 16-363 F F H OCH₂C≡CCH₂Cl 16-364 F Cl H OCH₂C≡CCH₂Cl 16-365 Cl F H OCH₂C≡CCH₂Cl 16-366 Cl Cl H OCH₂C≡CCH₂Cl 16-367 H F H OCH₂CN 16-368 H Cl H OCH₂CN 16-369 F F H OCH₂CN 16-370 F Cl H OCH₂CN 16-371 Cl F H OCH₂CN 16-372 Cl Cl H OCH₂CN 16-373 H F H OCH₂OCH₃ 16-374 H Cl H OCH₂OCH₃ 16-375 F F H OCH₂OCH₃

TABLE 202 X Y R¹ B 16-376 F Cl H OCH₂OCH₃ 16-377 Cl F H OCH₂OCH₃ 16-378 Cl Cl H OCH₂OCH₃ 16-379 H F H OCH₂OC₂H₅ 16-380 H Cl H OCH₂OC₂H₅ 16-381 F F H OCH₂OC₂H₅ 16-382 F Cl H OCH₂OC₂H₅ 16-383 Cl F H OCH₂OC₂H₅ 16-384 Cl Cl H OCH₂OC₂H₅ 16-385 H F H OCH₂SCH₃ 16-386 H Cl H OCH₂SCH₃ 16-387 F F H OCH₂SCH₃ 16-388 F Cl H OCH₂SCH₃ 16-389 Cl F H OCH₂SCH₃ 16-390 Cl Cl H OCH₂SCH₃ 16-391 H F H OCH₂COOH 16-392 H Cl H OCH₂COOH 16-393 F F H OCH₂COOH 16-394 F Cl H OCH₂COOH 16-395 Cl F H OCH₂COOH 16-396 Cl Cl H OCH₂COOH 16-397 H F H OCH₂COOCH₃ 16-398 H Cl H OCH₂COOCH₃ 16-399 F F H OCH₂COOCH₃ 16-400 F Cl H OCH₂COOCH₃

TABLE 203 X Y R¹ B 16-401 Cl F H OCH₂COOCH₃ 16-402 Cl Cl H OCH₂COOCH₃ 16-403 H F H OCH₂COOC₂H₅ 16-404 H Cl H OCH₂COOC₂H₅ 16-405 F F H OCH₂COOC₂H₅ 16-406 F Cl H OCH₂COOC₂H₅ 16-407 Cl F H OCH₂COOC₂H₅ 16-408 Cl Cl H OCH₂COOC₂H₅ 16-409 H F H OCH₂COOnC₃H₇ 16-410 H Cl H OCH₂COOnC₃H₇ 16-411 F F H OCH₂COOnC₃H₇ 16-412 F Cl H OCH₂COOnC₃H₇ 16-413 Cl F H OCH₂COOnC₃H₇ 16-414 Cl Cl H OCH₂COOnC₃H₇ 16-415 H F H OCH₂COOnC₄H₉ 16-416 H Cl H OCH₂COOnC₄H₉ 16-417 F F H OCH₂COOnC₄H₉ 16-418 F Cl H OCH₂COOnC₄H₉ 16-419 Cl F H OCH₂COOnC₄H₉ 16-420 Cl Cl H OCH₂COOnC₄H₉ 16-421 H F H OCH₂COOnC₅H₁₁ 16-422 H Cl H OCH₂COOnC₅H₁₁ 16-423 F F H OCH₂COOnC₅H₁₁ 16-424 F Cl H OCH₂COOnC₅H₁₁ 16-425 Cl F H OCH₂COOnC₅H₁₁

TABLE 204 X Y R¹ B 16-426 Cl Cl H OCH₂COOnC₅H₁₁ 16-427 H F H OCH₂COOiC₃H₇ 16-428 H Cl H OCH₂COOiC₃H₇ 16-429 F F H OCH₂COOiC₃H₇ 16-430 F Cl H OCH₂COOiC₃H₇ 16-431 Cl F H OCH₂COOiC₃H₇ 16-432 Cl Cl H OCH₂COOiC₃H₇ 16-433 H F H OCH₂COOcC₅H₉ 16-434 H Cl H OCH₂COOcC₅H₉ 16-435 F F H OCH₂COOcC₅H₉ 16-436 F Cl H OCH₂COOcC₅H₉ 16-437 Cl F H OCH₂COOcC₅H₉ 16-438 Cl Cl H OCH₂COOcC₅H₉ 16-439 H F H OCH₂COOcC₆H₁₁ 16-440 H Cl H OCH₂COOcC₆H₁₁ 16-441 F F H OCH₂COOcC₆H₁₁ 16-442 F Cl H OCH₂COOcC₆H₁₁ 16-443 Cl F H OCH₂COOcC₆H₁₁ 16-444 Cl Cl H OCH₂COOcC₆H₁₁ 16-445 H F H OCH(CH₃)COOH 16-446 H Cl H OCH(CH₃)COOH 16-447 F F H OCH(CH₃)COOH 16-448 F Cl H OCH(CH₃)COOH 16-449 Cl F H OCH(CH₃)COOH 16-450 Cl Cl H OCH(CH₃)COOH

TABLE 205 X Y R¹ B 16-451 H F H OCH(CH₃)COOCH₃ 16-452 H Cl H OCH(CH₃)COOCH₃ 16-453 F F H OCH(CH₃)COOCH₃ 16-454 F Cl H OCH(CH₃)COOCH₃ 16-455 Cl F H OCH(CH₃)COOCH₃ 16-456 Cl Cl H OCH(CH₃)COOCH₃ 16-457 H F H OCH(CH₃)COOC₂H₅ 16-458 H Cl H OCH(CH₃)COOC₂H₅ 16-459 F F H OCH(CH₃)COOC₂H₅ 16-460 F Cl H OCH(CH₃)COOC₂H₅ 16-461 Cl F H OCH(CH₃)COOC₂H₅ 16-462 Cl Cl H OCH(CH₃)COOC₂H₅ 16-463 H F H OCH(CH₃)COOnC₃H₇ 16-464 H CL H OCH(CH₃)COOnC₃H₇ 16-465 F F H OCH(CH₃)COOnC₃H₇ 16-466 F Cl H OCH(CH₃)COOnC₃H₇ 16-467 Cl F H OCH(CH₃)COOnC₃H₇ 16-468 Cl Cl H OCH(CH₃)COOnC₃H₇ 16-469 H F H OCH(CH₃)COOnC₄H₉ 16-470 H Cl H OCH(CH₃)COOnC₄H₉ 16-471 F F H OCH(CH₃)COOnC₄H₉ 16-472 F Cl H OCH(CH₃)COOnC₄H₉ 16-473 Cl F H OCH(CH₃)COOnC₄H₉ 16-474 Cl Cl H OCH(CH₃)COOnC₄H₉ 16-475 H F H OCH(CH₃)COOnC₅H₁₁

TABLE 206 X Y R¹ B 16-476 H Cl H OCH(CH₃)COOnC₅H₁₁ 16-477 F F H OCH(CH₃)COOnC₅H₁₁ 16-478 F Cl H OCH(CH₃)COOnC₅H₁₁ 16-479 Cl F H OCH(CH₃)COOnC₅H₁₁ 16-480 Cl Cl H OCH(CH₃)COOnC₅H₁₁ 16-481 H F H OCH(CH₃)COOiC₃H₇ 16-482 H Cl H OCH(CH₃)COOiC₃H₇ 16-483 F F H OCH(CH₃)COOiC₃H₇ 16-484 F Cl H OCH(CH₃)COOiC₃H₇ 16-485 Cl F H OCH(CH₃)COOiC₃H₇ 16-486 Cl Cl H OCH(CH₃)COOiC₃H₇ 16-487 H F H OCH(CH₃)COOcC₅H₉ 16-488 H CL H OCH(CH₃)COOcC₅H₉ 16-489 F F H OCH(CH₃)COOcC₅H₉ 16-490 F Cl H OCH(CH₃)COOcC₅H₉ 16-491 Cl F H OCH(CH₃)COOcC₅H₉ 16-492 Cl Cl H OCH(CH₃)COOcC₅H₉ 16-493 H F H OCH(CH₃)COOcC₆H₁₁ 16-494 H Cl H OCH(CH₃)COOcC₆H₁₁ 16-495 F F H OCH(CH₃)COOcC₆H₁₁ 16-496 F Cl H OCH(CH₃)COOcC₆H₁₁ 16-497 Cl F H OCH(CH₃)COOcC₆H₁₁ 16-498 Cl Cl H OCH(CH₃)COOcC₆H₁₁ 16-499 H F H OCH₂CONH₂ 16-500 H Cl H OCH₂CONH₂

TABLE 207 X Y R¹ B 16-501 F F H OCH₂CONH₂ 16-502 F Cl H OCH₂CONH₂ 16-503 Cl F H OCH₂CONH₂ 16-504 Cl Cl H OCH₂CONH₂ 16-505 H F H OCH₂CONHCH₃ 16-506 H Cl H OCH₂CONHCH₃ 16-507 F F H OCH₂CONHCH₃ 16-508 F Cl H OCH₂CONHCH₃ 16-509 Cl F H OCH₂CONHCH₃ 16-510 Cl Cl H OCH₂CONHCH₃ 16-511 H F H OCH₂CON(CH₃)₂ 16-512 H Cl H OCH₂CON(CH₃)₂ 16-513 F F H OCH₂CON(CH₃)₂ 16-514 F Cl H OCH₂CON(CH₃)₂ 16-515 Cl F H OCH₂CON(CH₃)₂ 16-516 Cl Cl H OCH₂CON(CH₃)₂ 16-517 H F H OCH₂CON(C₂H₅)₂ 16-518 H Cl H OCH₂CON(C₂H₅)₂ 16-519 F F H OCH₂CON(C₂H₅)₂ 16-520 F Cl H OCH₂CON(C₂H₅)₂ 16-521 Cl F H OCH₂CON(C₂H₅)₂ 16-522 Cl Cl H OCH₂CON(C₂H₅)₂ 16-523 H F H OCH₂CON(CH₃)C₂H₅ 16-524 H Cl H OCH₂CON(CH₃)C₂H₅ 16-525 F F H OCH₂CON(CH₃)C₂H₅

TABLE 208 X Y R¹ B 16-526 F Cl H OCH₂CON(CH₃)C₂H₅ 16-527 Cl F H OCH₂CON(CH₃)C₂H₅ 16-528 Cl Cl H OCH₂CON(CH₃)C₂H₅ 16-529 H F H OCH₂CON(tetramethylene) 16-530 H Cl H OCH₂CON(tetramethylene) 16-531 F F H OCH₂CON(tetramethylene) 16-532 F Cl H OCH₂CON(tetramethylene) 16-533 Cl F H OCH₂CON(tetramethylene) 16-534 Cl Cl H OCH₂CON(tetramethylene) 16-535 H F H OCH₂CON(pentamethylene) 16-536 H Cl H OCH₂CON(pentamethylene) 16-537 F F H OCH₂CON(pentamethylene) 16-538 F Cl H OCH₂CON(pentamethylene) 16-539 Cl F H OCH₂CON(pentamethylene) 16-540 Cl Cl H OCH₂CON(pentamethylene) 16-541 H F H OCH₂CON(ethyleneoxyethylene) 16-542 H Cl H OCH₂CON(ethyleneoxyethylene) 16-543 F F H OCH₂CON(ethyleneoxyethylene) 16-544 F Cl H OCH₂CON(ethyleneoxyethylene) 16-545 Cl F H OCH₂CON(ethyleneoxyethylene) 16-546 Cl Cl H OCH₂CON(ethyleneoxyethylene) 16-547 H F H OCH(CH₃)CONH₂ 16-548 H Cl H OCH(CH₃)CONH₂ 16-549 F F H OCH(CH₃)CONH₂ 16-550 F Cl H OCH(CH₃)CONH₂

TABLE 209 X Y R¹ B 16-551 Cl F H OCH(CH₃)CONH₂ 16-552 Cl Cl H OCH(CH₃)CONH₂ 16-553 H F H OCH(CH₃)CONHCH₃ 16-554 H Cl H OCH(CH₃)CONHCH₃ 16-555 F F H OCH(CH₃)CONHCH₃ 16-556 F Cl H OCH(CH₃)CONHCH₃ 16-557 Cl F H OCH(CH₃)CONHCH₃ 16-558 Cl Cl H OCH(CH₃)CONHCH₃ 16-559 H F H OCH(CH₃)CON(CH₃)₂ 16-560 H Cl H OCH(CH₃)CON(CH₃)₂ 16-561 F F H OCH(CH₃)CON(CH₃)₂ 16-562 F Cl H OCH(CH₃)CON(CH₃)₂ 16-563 Cl F H OCH(CH₃)CON(CH₃)₂ 16-564 Cl Cl H OCH(CH₃)CON(CH₃)₂ 16-565 H F H OCH(CH₃)CON(C₂H₅)₂ 16-566 H Cl H OCH(CH₃)CON(C₂H₅)₂ 16-567 F F H OCH(CH₃)CON(C₂H₅)₂ 16-568 F Cl H OCH(CH₃)CON(C₂H₅)₂ 16-569 Cl F H OCH(CH₃)CON(C₂H₅)₂ 16-570 Cl Cl H OCH(CH₃)CON(C₂H₅)₂ 16-571 H F H OCH(CH₃)CON(CH₃)C₂H₅ 16-572 H Cl H OCH(CH₃)CON(CH₃)C₂H₅ 16-573 F F H OCH(CH₃)CON(CH₃)C₂H₅ 16-574 F Cl H OCH(CH₃)CON(CH₃)C₂H₅ 16-575 Cl F H OCH(CH₃)CON(CH₃)C₂H₅

TABLE 210 X Y R¹ B 16-576 Cl Cl H OCH(CH₃)CON(CH₃)C₂H₅ 16-577 H F H OCH(CH₃)CON(tetramethylene) 16-578 H Cl H OCH(CH₃)CON(tetramethylene) 16-579 F F H OCH(CH₃)CON(tetramethylene) 16-580 F Cl H OCH(CH₃)CON(tetramethylene) 16-581 Cl F H OCH(CH₃)CON(tetramethylene) 16-582 Cl Cl H OCH(CH₃)CON(tetramethylene) 16-583 H F H OCH(CH₃)CON(pentamethylene) 16-584 H Cl H OCH(CH₃)CON(pentamethylene) 16-585 F F H OCH(CH₃)CON(pentamethylene) 16-586 F Cl H OCH(CH₃)CON(pentamethylene) 16-587 Cl F H OCH(CH₃)CON(pentamethylene) 16-588 Cl Cl H OCH(CH₃)CON(pentamethylene) 16-589 H F H OCH(CH₃)CON(ethyleneoxyethylene) 16-590 H Cl H OCH(CH₃)CON(ethyleneoxyethylene) 16-591 F F H OCH(CH₃)CON(ethyleneoxyethylene) 16-592 F Cl H OCH(CH₃)CON(ethyleneoxyethylene) 16-593 Cl F H OCH(CH₃)CON(ethyleneoxyethylene) 16-594 Cl Cl H OCH(CH₃)CON(ethyleneoxyethylene) 16-595 H F H OCH₂COON(CH₃)₂ 16-596 H Cl H OCH₂COON(CH₃)₂ 16-597 F F H OCH₂COON(CH₃)₂ 16-598 F Cl H OCH₂COON(CH₃)₂ 16-599 Cl F H OCH₂COON(CH₃)₂ 16-600 Cl Cl H OCH₂COON(CH₃)₂

TABLE 211 X Y R¹ B 16-601 H F H OCH₂COON(C₂H₅)₂ 16-602 H Cl H OCH₂COON(C₂H₅)₂ 16-603 F F H OCH₂COON(C₂H₅)₂ 16-604 F Cl H OCH₂COON(C₂H₅)₂ 16-605 Cl F H OCH₂COON(C₂H₅)₂ 16-606 Cl Cl H OCH₂COON(C₂H₅)₂ 16-607 H F H OCH(CH₃)COON(CH₃)₂ 16-608 H Cl H OCH(CH₃)COON(CH₃)₂ 16-609 F F H OCH(CH₃)COON(CH₃)₂ 16-610 F Cl H OCH(CH₃)COON(CH₃)₂ 16-611 Cl F H OCH(CH₃)COON(CH₃)₂ 16-612 Cl Cl H OCH(CH₃)COON(CH₃)₂ 16-613 H F H OCH(CH₃)COON(C₂H₅)₂ 16-614 H Cl H OCH(CH₃)COON(C₂H₅)₂ 16-615 F F H OCH(CH₃)COON(C₂H₅)₂ 16-616 F Cl H OCH(CH₃)COON(C₂H₅)₂ 16-617 Cl F H OCH(CH₃)COON(C₂H₅)₂ 16-618 Cl Cl H OCH(CH₃)COON(C₂H₅)₂ 16-619 H F H SCH₃ 16-620 H Cl H SCH₃ 16-621 F F H SCH₃ 16-622 F Cl H SCH₃ 16-623 Cl F H SCH₃ 16-624 Cl Cl H SCH₃ 16-625 H F H SC₂H₅

TABLE 212 X Y R¹ B 16-626 H Cl H SC₂H₅ 16-627 F F H SC₂H₅ 16-628 F Cl H SC₂H₅ 16-629 Cl F H SC₂H₅ 16-630 Cl Cl H SC₂H₅ 16-631 H F H SiC₃H₇ 16-632 H Cl H SiC₃H₇ 16-633 F F H SiC₃H₇ 16-634 F Cl H SiC₃H₇ 16-635 Cl F H SiC₃H₇ 16-636 Cl Cl H SiC₃H₇ 16-637 H F H SnC₃H₇ 16-638 H Cl H SnC₃H₇ 16-639 F F H SnC₃H₇ 16-640 F Cl H SnC₃H₇ 16-641 Cl F H SnC₃H₇ 16-642 Cl Cl H SnC₃H₇ 16-643 H F H SCH₂CH₂Cl 16-644 H Cl H SCH₂CH₂Cl 16-645 F F H SCH₂CH₂Cl 16-646 F Cl H SCH₂CH₂Cl 16-647 Cl F H SCH₂CH₂Cl 16-648 Cl Cl H SCH₂CH₂Cl 16-649 H F H ScC₅H₉ 16-650 H Cl H ScC₅H₉

TABLE 213 X Y R¹ B 16-651 F F H ScC₅H₉ 16-652 F Cl H ScC₅H₉ 16-653 Cl F H ScC₅H₉ 16-654 Cl Cl H ScC₅H₉ 16-655 H F H ScC₆H₁₁ 16-656 H Cl H ScC₆H₁₁ 16-657 F F H ScC₆H₁₁ 16-658 F Cl H ScC₆H₁₁ 16-659 Cl F H ScC₆H₁₁ 16-660 Cl Cl H ScC₆H₁₁ 16-661 H F H SCH₂CH═CH₂ 16-662 H CL H SCH₂CH═CH₂ 16-663 F F H SCH₂CH═CH₂ 16-664 F Cl H SCH₂CH═CH₂ 16-665 Cl F H SCH₂CH═CH₂ 16-666 Cl Cl H SCH₂CH═CH₂ 16-667 H F H SCH₂CCl═CH₂ 16-668 H Cl H SCH₂CCl═CH₂ 16-669 F F H SCH₂CCl═CH₂ 16-670 F Cl H SCH₂CCl═CH₂ 16-671 Cl F H SCH₂CCl═CH₂ 16-672 Cl Cl H SCH₂CCl═CH₂ 16-673 H F H SCH₂CCl═CHCl 16-674 H Cl H SCH₂CCl═CHCl 16-675 F F H SCH₂CCl═CHCl

TABLE 214 X Y R¹ B 16-676 F Cl H SCH₂CCl═CHCl 16-677 Cl F H SCH₂CCl═CHCl 16-678 Cl Cl H SCH₂CCl═CHCl 16-679 H F H SCH(CH₃)CH═CH₂ 16-680 H Cl H SCH(CH₃)CH═CH₂ 16-681 F F H SCH(CH₃)CH═CH₂ 16-682 F Cl H SCH(CH₃)CH═CH₂ 16-683 Cl F H SCH(CH₃)CH═CH₂ 16-684 Cl Cl H SCH(CH₃)CH═CH₂ 16-685 H F H SCH₂C≡CH 16-686 H Cl H SCH₂C≡CH 16-687 F F H SCH₂C≡CH 16-688 F Cl H SCH₂C≡CH 16-689 Cl F H SCH₂C≡CH 16-690 Cl Cl H SCH₂C≡CH 16-691 H F H SCH(CH₃)C≡CH 16-692 H Cl H SCH(CH₃)C≡CH 16-693 F F H SCH(CH₃)C≡CH 16-694 F Cl H SCH(CH₃)C≡CH 16-695 Cl F H SCH(CH₃)C≡CH 16-696 Cl Cl H SCH(CH₃)C≡CH 16-697 H F H SCH₂COOH 16-698 H Cl H SCH₂COOH 16-699 F F H SCH₂COOH 16-700 F Cl H SCH₂COOH

TABLE 215 X Y R¹ B 16-701 Cl F H SCH₂COOH 16-702 Cl Cl H SCH₂COOH 16-703 H F H SCH₂COOCH₃ 16-704 H Cl H SCH₂COOCH₃ 16-705 F F H SCH₂COOCH₃ 16-706 F Cl H SCH₂COOCH₃ 16-707 Cl F H SCH₂COOCH₃ 16-708 Cl Cl H SCH₂COOCH₃ 16-709 H F H SCH₂COOC₂H₅ 16-710 H Cl H SCH₂COOC₂H₅ 16-711 F F H SCH₂COOC₂H₅ 16-712 F Cl H SCH₂COOC₂H₅ 16-713 Cl F H SCH₂COOC₂H₅ 16-714 Cl Cl H SCH₂COOC₂H₅ 16-715 H F H SCH₂COOnC₃H₇ 16-716 H Cl H SCH₂COOnC₃H₇ 16-717 F F H SCH₂COOnC₃H₇ 16-718 F Cl H SCH₂COOnC₃H₇ 16-719 Cl F H SCH₂COOnC₃H₇ 16-720 Cl Cl H SCH₂COOnC₃H₇ 16-721 H F H SCH₂COOnC₄H₉ 16-722 H Cl H SCH₂COOnC₄H₉ 16-723 F F H SCH₂COOnC₄H₉ 16-724 F Cl H SCH₂COOnC₄H₉ 16-725 Cl F H SCH₂COOnC₄H₉

TABLE 216 X Y R¹ B 16-726 Cl Cl H SCH₂COOnC₄H₉ 16-727 H F H SCH₂COOnC₅H₁₁ 16-728 H Cl H SCH₂COOnC₅H₁₁ 16-729 F F H SCH₂COOnC₅H₁₁ 16-730 F Cl H SCH₂COOnC₅H₁₁ 16-731 Cl F H SCH₂COOnC₅H₁₁ 16-732 Cl Cl H SCH₂COOnC₅H₁₁ 16-733 H F H SCH₂COOiC₃H₇ 16-734 H Cl H SCH₂COOiC₃H₇ 16-735 F F H SCH₂COOiC₃H₇ 16-736 F Cl H SCH₂COOiC₃H₇ 16-737 Cl F H SCH₂COOiC₃H₇ 16-738 Cl Cl H SCH₂COOiC₃H₇ 16-739 H F H SCH₂COOcC₅H₉ 16-740 H Cl H SCH₂COOcC₅H₉ 16-741 F F H SCH₂COOcC₅H₉ 16-742 F Cl H SCH₂COOcC₅H₉ 16-743 Cl F H SCH₂COOcC₅H₉ 16-744 Cl Cl H SCH₂COOcC₅H₉ 16-745 H F H SCH₂COOcC₆H₁₁ 16-746 H Cl H SCH₂COOcC₆H₁₁ 16-747 F F H SCH₂COOcC₆H₁₁ 16-748 F Cl H SCH₂COOcC₆H₁₁ 16-749 Cl F H SCH₂COOcC₆H₁₁ 16-750 Cl Cl H SCH₂COOcC₆H₁₁

TABLE 217 X Y R¹ B 16-751 H F H SCH(CH₃)COOH 16-752 H Cl H SCH(CH₃)COOH 16-753 F F H SCH(CH₃)COOH 16-754 F Cl H SCH(CH₃)COOH 16-755 Cl F H SCH(CH₃)COOH 16-756 Cl Cl H SCH(CH₃)COOH 16-757 H F H SCH(CH₃)COOCH₃ 16-758 H Cl H SCH(CH₃)COOCH₃ 16-759 F F H SCH(CH₃)COOCH₃ 16-760 F Cl H SCH(CH₃)COOCH₃ 16-761 Cl F H SCH(CH₃)COOCH₃ 16-762 Cl Cl H SCH(CH₃)COOCH₃ 16-763 H F H SCH(CH₃)COOC₂H₅ 16-764 H Cl H SCH(CH₃)COOC₂H₅ 16-765 F F H SCH(CH₃)COOC₂H₅ 16-766 F Cl H SCH(CH₃)COOC₂H₅ 16-767 Cl F H SCH(CH₃)COOC₂H₅ 16-768 Cl Cl H SCH(CH₃)COOC₂H₅ 16-769 H F H SCH(CH₃)COOnC₃H₇ 16-770 H Cl H SCH(CH₃)COOnC₃H₇ 16-771 F F H SCH(CH₃)COOnC₃H₇ 16-772 F Cl H SCH(CH₃)COOnC₃H₇ 16-773 Cl F H SCH(CH₃)COOnC₃H₇ 16-774 Cl Cl H SCH(CH₃)COOnC₃H₇ 16-775 H F H SCH(CH₃)COOnC₄H₉

TABLE 218 X Y R¹ B 16-776 H Cl H SCH(CH₃)COOnC₄H₉ 16-777 F F H SCH(CH₃)COOnC₄H₉ 16-778 F Cl H SCH(CH₃)COOnC₄H₉ 16-779 Cl F H SCH(CH₃)COOnC₄H₉ 16-780 Cl Cl H SCH(CH₃)COOnC₄H₉ 16-781 H F H SCH(CH₃)COOnC₅H₁₁ 16-782 H Cl H SCH(CH₃)COOnC₅H₁₁ 16-783 F F H SCH(CH₃)COOnC₅H₁₁ 16-784 F Cl H SCH(CH₃)COOnC₅H₁₁ 16-785 Cl F H SCH(CH₃)COOnC₅H₁₁ 16-786 Cl Cl H SCH(CH₃)COOnC₅H₁₁ 16-787 H F H SCH(CH₃)COOiC₃H₇ 16-788 H Cl H SCH(CH₃)COOiC₃H₇ 16-789 F F H SCH(CH₃)COOiC₃H₇ 16-790 F Cl H SCH(CH₃)COOiC₃H₇ 16-791 Cl F H SCH(CH₃)COOiC₃H₇ 16-792 Cl Cl H SCH(CH₃)COOiC₃H₇ 16-793 H F H SCH(CH₃)COOcC₅H₉ 16-794 H Cl H SCH(CH₃)COOcC₅H₉ 16-795 F F H SCH(CH₃)COOcC₅H₉ 16-796 F Cl H SCH(CH₃)COOcC₅H₉ 16-797 Cl F H SCH(CH₃)COOcC₅H₉ 16-798 Cl Cl H SCH(CH₃)COOcC₅H₉ 16-799 H F H SCH(CH₃)COOcC₆H₁₁ 16-800 H Cl H SCH(CH₃)COOcC₆H₁₁

TABLE 219 X Y R¹ B 16-801 F F H SCH(CH₃)COOcC₆H₁₁ 16-802 F Cl H SCH(CH₃)COOcC₆H₁₁ 16-803 Cl F H SCH(CH₃)COOcC₆H₁₁ 16-804 Cl Cl H SCH(CH₃)COOcC₆H₁₁ 16-805 H F H SCH₂CONH₂ 16-806 H Cl H SCH₂CONH₂ 16-807 F F H SCH₂CONH₂ 16-808 F Cl H SCH₂CONH₂ 16-809 Cl F H SCH₂CONH₂ 16-810 Cl Cl H SCH₂CONH₂ 16-811 H F H SCH₂CONHCH₃ 16-812 H Cl H SCH₂CONHCH₃ 16-813 F F H SCH₂CONHCH₃ 16-814 F Cl H SCH₂CONHCH₃ 16-815 Cl F H SCH₂CONHCH₃ 16-816 Cl Cl H SCH₂CONHCH₃ 16-817 H F H SCH₂CON(CH₃)₂ 16-818 H Cl H SCH₂CON(CH₃)₂ 16-819 F F H SCH₂CON(CH₃)₂ 16-820 F Cl H SCH₂CON(CH₃)₂ 16-821 Cl F H SCH₂CON(CH₃)₂ 16-822 Cl Cl H SCH₂CON(CH₃)₂ 16-823 H F H SCH₂CON(C₂H₅)₂ 16-824 H Cl H SCH₂CON(C₂H₅)₂ 16-825 F F H SCH₂CON(C₂H₅)₂

TABLE 220 X Y R¹ B 16-826 F Cl H SCH₂CON(C₂H₅)₂ 16-827 Cl F H SCH₂CON(C₂H₅)₂ 16-828 Cl Cl H SCH₂CON(C₂H₅)₂ 16-829 H F H SCH₂CON(CH₃)C₂H₅ 16-830 H Cl H SCH₂CON(CH₃)C₂H₅ 16-831 F F H SCH₂CON(CH₃)C₂H₅ 16-832 F Cl H SCH₂CON(CH₃)C₂H₅ 16-833 Cl F H SCH₂CON(CH₃)C₂H₅ 16-834 Cl Cl H SCH₂CON(CH₃)C₂H₅ 16-835 H F H SCH₂CON(tetramethylene) 16-836 H Cl H SCH₂CON(tetramethylene) 16-837 F F H SCH₂CON(tetramethylene) 16-838 F Cl H SCH₂CON(tetramethylene) 16-839 Cl F H SCH₂CON(tetramethylene) 16-840 Cl Cl H SCH₂CON(tetramethylene) 16-841 H F H SCH₂CON(pentamethylene) 16-842 H Cl H SCH₂CON(pentamethylene) 16-843 F F H SCH₂CON(pentamethylene) 16-844 F Cl H SCH₂CON(pentamethylene) 16-845 Cl F H SCH₂CON(pentamethylene) 16-846 Cl Cl H SCH₂CON(pentamethylene) 16-847 H F H SCH₂CON(ethyleneoxyethylene) 16-848 H Cl H SCH₂CON(ethyleneoxyethylene) 16-849 F F H SCH₂CON(ethyleneoxyethylene) 16-850 F Cl H SCH₂CON(ethyleneoxyethylene)

TABLE 221 X Y R¹ B 16-851 Cl F H SCH₂CON(ethyleneoxyethylene) 16-852 Cl Cl H SCH₂CON(ethyleneoxyethylene) 16-853 H F H SCH(CH₃)CONH₂ 16-854 H Cl H SCH(CH₃)CONH₂ 16-855 F F H SCH(CH₃)CONH₂ 16-856 F Cl H SCH(CH₃)CONH₂ 16-857 Cl F H SCH(CH₃)CONH₂ 16-858 Cl Cl H SCH(CH₃)CONH₂ 16-859 H F H SCH(CH₃)CONHCH₃ 16-860 H Cl H SCH(CH₃)CONHCH₃ 16-861 F F H SCH(CH₃)CONHCH₃ 16-862 F Cl H SCH(CH₃)CONHCH₃ 16-863 Cl F H SCH(CH₃)CONHCH₃ 16-864 Cl Cl H SCH(CH₃)CONHCH₃ 16-865 H F H SCH(CH₃)CON(CH₃)₂ 16-866 H Cl H SCH(CH₃)CON(CH₃)₂ 16-867 F F H SCH(CH₃)CON(CH₃)₂ 16-868 F Cl H SCH(CH₃)CON(CH₃)₂ 16-869 Cl F H SCH(CH₃)CON(CH₃)₂ 16-870 Cl Cl H SCH(CH₃)CON(CH₃)₂ 16-871 H F H SCH(CH₃)CON(C₂H₅)₂ 16-872 H Cl H SCH(CH₃)CON(C₂H₅)₂ 16-873 F F H SCH(CH₃)CON(C₂H₅)₂ 16-874 F Cl H SCH(CH₃)CON(C₂H₅)₂ 16-875 Cl F H SCH(CH₃)CON(C₂H₅)₂

TABLE 222 X Y R¹ B 16-876 Cl Cl H SCH(CH₃)CON(C₂H₅)₂ 16-877 H F H SCH(CH₃)CON(CH₃)C₂H₅ 16-878 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 16-879 F F H SCH(CH₃)CON(CH₃)C₂H₅ 16-880 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 16-881 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 16-882 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 16-883 H F H SCH(CH₃)CON(CH₃)C₂H₅ 16-884 H Cl H SCH(CH₃)CON(CH₃)C₂H₅ 16-885 F F H SCH(CH₃)CON(CH₃)C₂H₅ 16-886 F Cl H SCH(CH₃)CON(CH₃)C₂H₅ 16-887 Cl F H SCH(CH₃)CON(CH₃)C₂H₅ 16-888 Cl Cl H SCH(CH₃)CON(CH₃)C₂H₅ 16-889 H F H SCH(CH₃)CON(tetramethylene) 16-890 H Cl H SCH(CH₃)CON(tetramethylene) 16-891 F F H SCH(CH₃)CON(tetramethylene) 16-892 F Cl H SCH(CH₃)CON(tetramethylene) 16-893 Cl F H SCH(CH₃)CON(tetramethylene) 16-894 Cl Cl H SCH(CH₃)CON(tetramethylene) 16-895 H F H SCH(CH₃)CON(pentamethylene) 16-896 H Cl H SCH(CH₃)CON(pentamethylene) 16-897 F F H SCH(CH₃)CON(pentamethylene) 16-898 F Cl H SCH(CH₃)CON(pentamethylene) 16-899 Cl F H SCH(CH₃)CON(pentamethylene) 16-900 Cl Cl H SCH(CH₃)CON(pentamethylene)

TABLE 223 X Y R¹ B 16-901 H F H SCH(CH₃)CON(ethyleneoxyethylene) 16-902 H Cl H SCH(CH₃)CON(ethyleneoxyethylene) 16-903 F F H SCH(CH₃)CON(ethyleneoxyethylene) 16-904 F Cl H SCH(CH₃)CON(ethyleneoxyethylene) 16-905 Cl F H SCH(CH₃)CON(ethyleneoxyethylene) 16-906 Cl Cl H SCH(CH₃)CON(ethyleneoxyethylene) 16-907 H F H SO₂OCH₃ 16-908 H Cl H SO₂OCH₃ 16-909 F F H SO₂OCH₃ 16-910 F Cl H SO₂OCH₃ 16-911 Cl F H SO₂OCH₃ 16-912 Cl Cl H SO₂OCH₃ 16-913 H F H SO₂OC₂H₅ 16-914 H Cl H SO₂OC₂H₅ 16-915 F F H SO₂OC₂H₅ 16-916 F Cl H SO₂OC₂H₅ 16-917 Cl F H SO₂OC₂H₅ 16-918 Cl Cl H SO₂OC₂H₅ 16-919 H F H SO₂OiC₃H₇ 16-920 H Cl H SO₂OiC₃H₇ 16-921 F F H SO₂OiC₃H₇ 16-922 F Cl H SO₂OiC₃H₇ 16-923 Cl F H SO₂OiC₃H₇ 16-924 Cl Cl H SO₂OiC₃H₇ 16-925 H F H SO₂OCH₂CH═CH₂

TABLE 224 X Y R¹ B 16-926 H Cl H SO₂OCH₂CH═CH₂ 16-927 F F H SO₂OCH₂CH═CH₂ 16-928 F Cl H SO₂OCH₂CH═CH₂ 16-929 Cl F H SO₂OCH₂CH═CH₂ 16-930 Cl Cl H SO₂OCH₂CH═CH₂ 16-931 H F H SO₂N(CH₃)₂ 16-932 H Cl H SO₂N(CH₃)₂ 16-933 F F H SO₂N(CH₃)₂ 16-934 F Cl H SO₂N(CH₃)₂ 16-935 Cl F H SO₂N(CH₃)₂ 16-936 Cl Cl H SO₂N(CH₃)₂ 16-937 H F H SO₂N(C₂H₅)₂ 16-938 H Cl H SO₂N(C₂H₅)₂ 16-939 F F H SO₂N(C₂H₅)₂ 16-940 F Cl H SO₂N(C₂H₅)₂ 16-941 Cl F H SO₂N(C₂H₅)₂ 16-942 Cl Cl H SO₂N(C₂H₅)₂ 16-943 H F H COOH 16-944 H Cl H COOH 16-945 F F H COOH 16-946 F Cl H COOH 16-947 Cl F H COOH 16-948 Cl Cl H COOH 16-949 H F H COOCH₃ 16-950 H Cl H COOCH₃

TABLE 225 X Y R¹ B 16-951 F F H COOCH₃ 16-952 F Cl H COOCH₃ 16-953 Cl F H COOCH₃ 16-954 Cl Cl H COOCH₃ 16-955 H F H COOC₂H₅ 16-956 H Cl H COOC₂H₅ 16-957 F F H COOC₂H₅ 16-958 F Cl H COOC₂H₅ 16-959 Cl F H COOC₂H₅ 16-960 Cl Cl H COOC₂H₅ 16-961 H F H COOnC₃H₇ 16-962 H Cl H COOnC₃H₇ 16-963 F F H COOnC₃H₇ 16-964 F Cl H COOnC₃H₇ 16-965 Cl F H COOnC₃H₇ 16-966 Cl Cl H COOnC₃H₇ 16-967 H F H COOnC₄H₉ 16-968 H Cl H COOnC₄H₉ 16-969 F F H COOnC₄H₉ 16-970 F Cl H COOnC₄H₉ 16-971 Cl F H COOnC₄H₉ 16-972 Cl Cl H COOnC₄H₉ 16-973 H F H COOnC₅H₁₁ 16-974 H Cl H COOnC₅H₁₁ 16-975 F F H COOnC₅H₁₁

TABLE 226 X Y R¹ B 16-976 F Cl H COOnC₅H₁₁ 16-977 Cl F H COOnC₅H₁₁ 16-978 Cl Cl H COOnC₅H₁₁ 16-979 H F H COOiC₃H₇ 16-980 H Cl H COOiC₃H₇ 16-981 F F H COOiC₃H₇ 16-982 F Cl H COOiC₃H₇ 16-983 Cl F H COOiC₃H₇ 16-984 Cl Cl H COOiC₃H₇ 16-985 H F H COOcC₅H₉ 16-986 H Cl H COOcC₅H₉ 16-987 F F H COOcC₅H₉ 16-988 F Cl H COOcC₅H₉ 16-989 Cl F H COOcC₅H₉ 16-990 Cl Cl H COOcC₅H₉ 16-991 H F H COOcC₆H₁₁ 16-992 H Cl H COOcC₆H₁₁ 16-993 F F H COOcC₆H₁₁ 16-994 F Cl H COOcC₆H₁₁ 16-995 Cl F H COOcC₆H₁₁ 16-996 Cl Cl H COOcC₆H₁₁ 16-997 H F H COOCH₂C₆H₅ 16-998 H Cl H COOCH₂C₆H₅ 16-999 F F H COOCH₂C₆H₅  16-1000 F Cl H COOCH₂C₆H₅

TABLE 227 X Y R¹ B 16-1001 Cl F H COOCH₂C₆H₅ 16-1002 Cl Cl H COOCH₂C₆H₅ 16-1003 H F H COOCH₂CH₂Cl 16-1004 H Cl H COOCH₂CH₂Cl 16-1005 F F H COOCH₂CH₂Cl 16-1006 F Cl H COOCH₂CH₂Cl 16-1007 Cl F H COOCH₂CH₂Cl 16-1008 Cl Cl H COOCH₂CH₂Cl 16-1009 H F H COOCH₂CH₂Br 16-1010 H Cl H COOCH₂CH₂Br 16-1011 F F H COOCH₂CH₂Br 16-1012 F Cl H COOCH₂CH₂Br 16-1013 Cl F H COOCH₂CH₂Br 16-1014 Cl Cl H COOCH₂CH₂Br 16-1015 H F H CONH₂ 16-1016 H Cl H CONH₂ 16-1017 F F H CONH₂ 16-1018 F Cl H CONH₂ 16-1019 Cl F H CONH₂ 16-1020 Cl Cl H CONH₂ 16-1021 H F H CONHCH₃ 16-1022 H Cl H CONHCH₃ 16-1023 F F H CONHCH₃ 16-1024 F Cl H CONHCH₃ 16-1025 Cl F H CONHCH₃

TABLE 228 X Y R¹ B 16-1026 Cl Cl H CONHCH₃ 16-1027 H F H CONHC₂H₅ 16-1028 H Cl H CONHC₂H₅ 16-1029 F F H CONHC₂H₅ 16-1030 F Cl H CONHC₂H₅ 16-1031 Cl F H CONHC₂H₅ 16-1032 Cl Cl H CONHC₂H₅ 16-1033 H F H CON(CH₃)₂ 16-1034 H Cl H CON(CH₃)₂ 16-1035 F F H CON(CH₃)₂ 16-1036 F Cl H CON(CH₃)₂ 16-1037 Cl F H CON(CH₃)₂ 16-1038 Cl Cl H CON(CH₃)₂ 16-1039 H F H CON(C₂H₅)₂ 16-1040 H Cl H CON(C₂H₅)₂ 16-1041 F F H CON(C₂H₅)₂ 16-1042 F Cl H CON(C₂H₅)₂ 16-1043 Cl F H CON(C₂H₅)₂ 16-1044 Cl Cl H CON(C₂H₅)₂ 16-1045 H F H CON(CH₃)(C₂H₅) 16-1046 H Cl H CON(CH₃)(C₂H₅) 16-1047 F F H CON(CH₃)(C₂H₅) 16-1048 F Cl H CON(CH₃)(C₂H₅) 16-1049 Cl F H CON(CH₃)(C₂H₅) 16-1050 Cl Cl H CON(CH₃)(C₂H₅)

TABLE 229 X Y R¹ B 16-1051 H F H COCH₃ 16-1052 H Cl H COCH₃ 16-1053 F F H COCH₃ 16-1054 F Cl H COCH₃ 16-1055 Cl F H COCH₃ 16-1056 Cl Cl H COCH₃ 16-1057 H F H COC₂H₅ 16-1058 H Cl H COC₂H₅ 16-1059 F F H COC₂H₅ 16-1060 F Cl H COC₂H₅ 16-1061 Cl F H COC₂H₅ 16-1062 Cl Cl H COC₂H₅ 16-1063 H F H COCH₂Cl 16-1064 H Cl H COCH₂Cl 16-1065 F F H COCH₂Cl 16-1066 F Cl H COCH₂Cl 16-1067 Cl F H COCH₂Cl 16-1068 Cl Cl H COCH₂Cl 16-1069 H F H CHO 16-1070 H Cl H CHO 16-1071 F F H CHO 16-1072 F Cl H CHO 16-1073 Cl F H CHO 16-1074 Cl Cl H CHO 16-1075 H F H CH₂CH₂COOH

TABLE 230 X Y R¹ B 16-1076 H Cl H CH₂CH₂COOH 16-1077 F F H CH₂CH₂COOH 16-1078 F Cl H CH₂CH₂COOH 16-1079 Cl F H CH₂CH₂COOH 16-1080 Cl Cl H CH₂CH₂COOH 16-1081 H F H CH₂CH₂COOCH₃ 16-1082 H Cl H CH₂CH₂COOCH₃ 16-1083 F F H CH₂CH₂COOCH₃ 16-1084 F Cl H CH₂CH₂COOCH₃ 16-1085 Cl F H CH₂CH₂COOCH₃ 16-1086 Cl Cl H CH₂CH₂COOCH₃ 16-1087 H F H CH₂CH₂COOC₂H₅ 16-1088 H Cl H CH₂CH₂COOC₂H₅ 16-1089 F F H CH₂CH₂COOC₂H₅ 16-1090 F Cl H CH₂CH₂COOC₂H₅ 16-1091 Cl F H CH₂CH₂COOC₂H₅ 16-1092 Cl Cl H CH₂CH₂COOC₂H₅ 16-1093 H F H CH₂CHClCOOCH₃ 16-1094 H Cl H CH₂CHClCOOCH₃ 16-1095 F F H CH₂CHClCOOCH₃ 16-1096 F Cl H CH₂CHClCOOCH₃ 16-1097 Cl F H CH₂CHClCOOCH₃ 16-1098 Cl Cl H CH₂CHClCOOCH₃ 16-1099 H F H CH₂CHClCOOC₂H₅ 16-1100 H Cl H CH₂CHClCOOC₂H₅

TABLE 231 X Y R¹ B 16-1101 F F H CH₂CHClCOOC₂H₅ 16-1102 F Cl H CH₂CHClCOOC₂H₅ 16-1103 Cl F H CH₂CHClCOOC₂H₅ 16-1104 Cl Cl H CH₂CHClCOOC₂H₅ 16-1105 H F H CH═CHCOOCH₃ 16-1106 H Cl H CH═CHCOOCH₃ 16-1107 F F H CH═CHCOOCH₃ 16-1108 F Cl H CH═CHCOOCH₃ 16-1109 Cl F H CH═CHCOOCH₃ 16-1110 Cl Cl H CH═CHCOOCH₃ 16-1111 H F H CH═CHCOOC₂H₅ 16-1112 H Cl H CH═CHCOOC₂H₅ 16-1113 F F H CH═CHCOOC₂H₅ 16-1114 F Cl H CH═CHCOOC₂H₅ 16-1115 Cl F H CH═CHCOOC₂H₅ 16-1116 Cl Cl H CH═CHCOOC₂H₅ 16-1117 H F H C(CH₃)═NOH 16-1118 H Cl H C(CH₃)═NOH 16-1119 F F H C(CH₃)═NOH 16-1120 F Cl H C(CH₃)═NOH 16-1121 Cl F H C(CH₃)═NOH 16-1122 Cl Cl H C(CH₃)═NOH 16-1123 H F H C(CH₃)═NOCH₃ 16-1124 H Cl H C(CH₃)═NOCH₃ 16-1125 F F H C(CH₃)═NOCH₃

TABLE 232 X Y R¹ B 16-1126 F Cl H C(CH₃)═NOCH₃ 16-1127 Cl F H C(CH₃)═NOCH₃ 16-1128 Cl Cl H C(CH₃)═NOCH₃ 16-1129 H F H C(CH₃)═NOC₂H₅ 16-1130 H Cl H C(CH₃)═NOC₂H₅ 16-1131 F F H C(CH₃)═NOC₂H₅ 16-1132 F Cl H C(CH₃)═NOC₂H₅ 16-1133 Cl F H C(CH₃)═NOC₂H₅ 16-1134 Cl Cl H C(CH₃)═NOC₂H₅ 16-1135 H F H C(CH₃)═NOiC₃H₇ 16-1136 H Cl H C(CH₃)═NOiC₃H₇ 16-1137 F F H C(CH₃)═NOiC₃H₇ 16-1138 F Cl H C(CH₃)═NOiC₃H₇ 16-1139 Cl F H C(CH₃)═NOiC₃H₇ 16-1140 Cl Cl H C(CH₃)═NOiC₃H₇ 16-1141 H F H C(CH₃)═NNH₂ 16-1142 H Cl H C(CH₃)═NNH₂ 16-1143 F F H C(CH₃)═NNH₂ 16-1144 F Cl H C(CH₃)═NNH₂ 16-1145 Cl F H C(CH₃)═NNH₂ 16-1146 Cl Cl H C(CH₃)═NNH₂ 16-1147 H F H C(CH₃)═NNHCH₃ 16-1148 H Cl H C(CH₃)═NNHCH₃ 16-1149 F F H C(CH₃)═NNHCH₃ 16-1150 F Cl H C(CH₃)═NNHCH₃

TABLE 233 X Y R¹ B 16-1151 Cl F H C(CH₃)═NNHCH₃ 16-1152 Cl Cl H C(CH₃)═NNHCH₃ 16-1153 H F H C(CH₃)═NN(CH₃)₂ 16-1154 H Cl H C(CH₃)═NN(CH₃)₂ 16-1155 F F H C(CH₃)═NN(CH₃)₂ 16-1156 F Cl H C(CH₃)═NN(CH₃)₂ 16-1157 Cl F H C(CH₃)═NN(CH₃)₂ 16-1158 Cl Cl H C(CH₃)═NN(CH₃)₂ 16-1159 H F H C(CH₃)═NNHC₂H₅ 16-1160 H Cl H C(CH₃)═NNHC₂H₅ 16-1161 F F H C(CH₃)═NNHC₂H₅ 16-1162 F Cl H C(CH₃)═NNHC₂H₅ 16-1163 Cl F H C(CH₃)═NNHC₂H₅ 16-1164 Cl Cl H C(CH₃)═NNHC₂H₅ 16-1165 H F H C(CH₃)═NN(C₂H₅)₂ 16-1166 H Cl H C(CH₃)═NN(C₂H₅)₂ 16-1167 F F H C(CH₃)═NN(C₂H₅)₂ 16-1168 F Cl H C(CH₃)═NN(C₂H₅)₂ 16-1169 Cl F H C(CH₃)═NN(C₂H₅)₂ 16-1170 Cl Cl H C(CH₃)═NN(C₂H₅)₂ 16-1171 H F H C(C₂H₅)═NNH₂ 16-1172 H Cl H C(C₂H₅)═NNH₂ 16-1173 F F H C(C₂H₅)═NNH₂ 16-1174 F Cl H C(C₂H₅)═NNH₂ 16-1175 Cl F H C(C₂H₅)═NNH₂

TABLE 234 X Y R¹ B 16-1176 Cl Cl H C(C₂H₅)═NNH₂ 16-1177 H F H C(C₂H₅)═NNHCH₃ 16-1178 H Cl H C(C₂H₅)═NNHCH₃ 16-1179 F F H C(C₂H₅)═NNHCH₃ 16-1180 F Cl H C(C₂H₅)═NNHCH₃ 16-1181 Cl F H C(C₂H₅)═NNHCH₃ 16-1182 Cl Cl H C(C₂H₅)═NNHCH₃ 16-1183 H F H C(C₂H₅)═NN(CH₃)₂ 16-1184 H Cl H C(C₂H₅)═NN(CH₃)₂ 16-1185 F F H C(C₂H₅)═NN(CH₃)₂ 16-1186 F Cl H C(C₂H₅)═NN(CH₃)₂ 16-1187 Cl F H C(C₂H₅)═NN(CH₃)₂ 16-1188 Cl Cl H C(C₂H₅)═NN(CH₃)₂ 16-1189 H F H C(C₂H₅)═NNHC₂H₅ 16-1190 H Cl H C(C₂H₅)═NNHC₂H₅ 16-1191 F F H C(C₂H₅)═NNHC₂H₅ 16-1192 F Cl H C(C₂H₅)═NNHC₂H₅ 16-1193 Cl F H C(C₂H₅)═NNHC₂H₅ 16-1194 Cl Cl H C(C₂H₅)═NNHC₂H₅ 16-1195 H F H C(C₂H₅)═NN(C₂H₅)₂ 16-1196 H Cl H C(C₂H₅)═NN(C₂H₅)₂ 16-1197 F F H C(C₂H₅)═NN(C₂H₅)₂ 16-1198 F Cl H C(C₂H₅)═NN(C₂H₅)₂ 16-1199 Cl F H C(C₂H₅)═NN(C₂H₅)₂ 16-1200 Cl Cl H C(C₂H₅)═NN(C₂H₅)₂

TABLE 235 X Y R¹ B 16-1201 H F H C(CH₃)(OCH₃)₂ 16-1202 H Cl H C(CH₃)(OCH₃)₂ 16-1203 F F H C(CH₃)(OCH₃)₂ 16-1204 F Cl H C(CH₃)(OCH₃)₂ 16-1205 Cl F H C(CH₃)(OCH₃)₂ 16-1206 Cl Cl H C(CH₃)(OCH₃)₂ 16-1207 H F H C(CH₃)(OC₂H₅)₂ 16-1208 H Cl H C(CH₃)(OC₂H₅)₂ 16-1209 F F H C(CH₃)(OC₂H₅)₂ 16-1210 F Cl H C(CH₃)(OC₂H₅)₂ 16-1211 Cl F H C(CH₃)(OC₂H₅)₂ 16-1212 Cl Cl H C(CH₃)(OC₂H₅)₂ 16-1213 H F H C(CH₃)(OiC₃H₇)₂ 16-1214 H Cl H C(CH₃)(OiC₃H₇)₂ 16-1215 F F H C(CH₃)(OiC₃H₇)₂ 16-1216 F Cl H C(CH₃)(OiC₃H₇)₂ 16-1217 Cl F H C(CH₃)(OiC₃H₇)₂ 16-1218 Cl Cl H C(CH₃)(OiC₃H₇)₂ 16-1219 H F H C(CH₃)(OCH₂CH₂O) 16-1220 H Cl H C(CH₃)(OCH₂CH₂O) 16-1221 F F H C(CH₃)(OCH₂CH₂O) 16-1222 F Cl H C(CH₃)(OCH₂CH₂O) 16-1223 Cl F H C(CH₃)(OCH₂CH₂O) 16-1224 Cl Cl H C(CH₃)(OCH₂CH₂O) 16-1225 H F H C(CH₃)(OCH₂CH₂CH₂O)

TABLE 236 X Y R¹ B 16-1226 H Cl H C(CH₃)(OCH₂CH₂CH₂O) 16-1227 F F H C(CH₃)(OCH₂CH₂CH₂O) 16-1228 F Cl H C(CH₃)(OCH₂CH₂CH₂O) 16-1229 Cl F H C(CH₃)(OCH₂CH₂CH₂O) 16-1230 Cl Cl H C(CH₃)(OCH₂CH₂CH₂O) 16-1231 H F H C(C₂H₅)(OCH₂CH₂O) 16-1232 H Cl H C(C₂H₅)(OCH₂CH₂O) 16-1233 F F H C(C₂H₅)(OCH₂CH₂O) 16-1234 F Cl H C(C₂H₅)(OCH₂CH₂O) 16-1235 Cl F H C(C₂H₅)(OCH₂CH₂O) 16-1236 Cl Cl H C(C₂H₅)(OCH₂CH₂O) 16-1237 H F H C(C₂H₅)(OCH₂CH₂CH₂O) 16-1238 H Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 16-1239 F F H C(C₂H₅)(OCH₂CH₂CH₂O) 16-1240 F Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 16-1241 Cl F H C(C₂H₅)(OCH₂CH₂CH₂O) 16-1242 Cl Cl H C(C₂H₅)(OCH₂CH₂CH₂O) 16-1243 H F H OCH₂CH(CH₃)₂ 16-1244 H Cl H OCH₂CH(CH₃)₂ 16-1245 F F H OCH₂CH(CH₃)₂ 16-1246 F Cl H OCH₂CH(CH₃)₂ 16-1247 Cl F H OCH₂CH(CH₃)₂ 16-1248 Cl Cl H OCH₂CH(CH₃)₂ 16-1249 H F H OCH₂CH₂F 16-1250 H Cl H OCH₂CH₂F

TABLE 237 X Y R¹ B 16-1251 F F H OCH₂CH₂F 16-1252 F Cl H OCH₂CH₂F 16-1253 Cl F H OCH₂CH₂F 16-1254 Cl Cl H OCH₂CH₂F 16-1255 H Cl H CH₂OH 16-1256 F Cl H CH₂OH 16-1257 H Cl H CH₂OCOCH₃ 16-1258 F Cl H CH₂OCOCH₃

Compounds of the general formula:

TABLE 238 X Z¹ n R¹ R⁴ R⁵ 17-1  H O 1 H H H 17-2  F O 1 H H H 17-3  H O 1 H H CH₃ 17-4  F O 1 H H CH₃ 17-5  H O 1 H H C₂H₅ 17-6  F O 1 H H C₂H₅ 17-7  H O 1 H H nC₃H₇ 17-8  F O 1 H H nC₃H₇ 17-9  H O 1 H H nC₄H₉ 17-10 F O 1 H H nC₄H₉ 17-11 H O 1 H H nC₅H₁₁ 17-12 F O 1 H H nC₅H₁₁ 17-13 H O 1 H H iC₃H₇ 17-14 F O 1 H H iC₃H₇ 17-15 H O 1 H H CH₂CH₂Cl 17-16 F O 1 H H CH₂CH₂Cl 17-17 H O 1 H H CH₂CH₂Br 17-18 F O 1 H H CH₂CH₂Br 17-19 H O 1 H H CH₂CH═CH₂ 17-20 F O 1 H H CH₂CH═CH₂ 17-21 H O 1 H H CH(CH₃)CH═CH₂ 17-22 F O 1 H H CH(CH₃)CH═CH₂ 17-23 H O 1 H H CH₂CCl═CH₂ 17-24 F O 1 H H CH₂CCl═CH₂ 17-25 H O 1 H H CH₂C≡CH

TABLE 239 X Z¹ n R¹ R⁴ R⁵ 17-26 F O 1 H H CH₂C≡CH 17-27 H O 1 H H CH(CH₃)C≡CH 17-28 F O 1 H H CH(CH₃)C≡CH 17-29 H O 1 H H CH₂CN 17-30 F O 1 H H CH₂CN 17-31 H O 1 H H CH₂OCH₃ 17-32 F O 1 H H CH₂OCH₃ 17-33 H O 1 H H CH₂OC₂H₅ 17-34 F O 1 H H CH₂OC₂H₅ 17-35 H O 1 H H CH₂COOH 17-36 F O 1 H H CH₂COOH 17-37 H O 1 H H CH₂COOCH₃ 17-38 F O 1 H H CH₂COOCH₃ 17-39 H O 1 H H CH₂COOC₂H₅ 17-40 F O 1 H H CH₂COOC₂H₅ 17-41 H O 1 H H CH₂COOnC₃H₇ 17-42 F O 1 H H CH₂COOnC₃H₇ 17-43 H O 1 H H CH₂COOnC₄H₉ 17-44 F O 1 H H CH₂COOnC₄H₉ 17-45 H O 1 H H CH₂COOnC₅H₁₁ 17-46 F O 1 H H CH₂COOnC₅H₁₁ 17-47 H O 1 H H CH₂COOiC₃H₇ 17-48 F O 1 H H CH₂COOiC₃H₇ 17-49 H O 1 H H CH₂COOcC₅H₉ 17-50 F O 1 H H CH₂COOcC₅H₉

TABLE 240 X Z¹ n R¹ R⁴ R⁵ 17-51 H O 1 H H CH₂COOcC₆H₁₁ 17-52 F O 1 H H CH₂COOcC₆H₁₁ 17-53 H O 1 H H CH(CH₃)COOH 17-54 F O 1 H H CH(CH₃)COOH 17-55 H O 1 H H CH(CH₃)COOCH₃ 17-56 F O 1 H H CH(CH₃)COOCH₃ 17-57 H O 1 H H CH(CH₃)COOC₂H₅ 17-58 F O 1 H H CH(CH₃)COOC₂H₅ 17-59 H O 1 H H CH(CH₃)COOnC₃H₇ 17-60 F O 1 H H CH(CH₃)COOnC₃H₇ 17-61 H O 1 H H CH(CH₃)COOnC₄H₉ 17-62 F O 1 H H CH(CH₃)COOnC₄H₉ 17-63 H O 1 H H CH(CH₃)COOnC₅H₁₁ 17-64 F O 1 H H CH(CH₃)COOnC₅H₁₁ 17-65 H O 1 H H CH(CH₃)COOiC₃H₇ 17-66 F O 1 H H CH(CH₃)COOiC₃H₇ 17-67 H O 1 H H CH(CH₃)COOcC₅H₉ 17-68 F O 1 H H CH(CH₃)COOcC₅H₉ 17-69 H O 1 H H CH(CH₃)COOcC₆H₁₁ 17-70 F O 1 H H CH(CH₃)COOcC₆H₁₁ 17-71 H O 1 H CH₃ H 17-72 F O 1 H CH₃ H 17-73 H O 1 H CH₃ CH₃ 17-74 F O 1 H CH₃ CH₃ 17-75 H O 1 H CH₃ C₂H₅

TABLE 241 X Z¹ n R¹ R⁴ R⁵ 17-76 F O 1 H CH₃ C₂H₅ 17-77 H O 1 H CH₃ nC₃H₇ 17-78 F O 1 H CH₃ nC₃H₇ 17-79 H O 1 H CH₃ nC₄H₉ 17-80 F O 1 H CH₃ nC₄H₉ 17-81 H O 1 H CH₃ nC₅H₁₁ 17-82 F O 1 H CH₃ nC₅H₁₁ 17-83 H O 1 H CH₃ iC₃H₇ 17-84 F O 1 H CH₃ iC₃H₇ 17-85 H O 1 H CH₃ CH₂CH₂Cl 17-86 F O 1 H CH₃ CH₂CH₂Cl 17-87 H O 1 H CH₃ CH₂CH₂Br 17-88 F O 1 H CH₃ CH₂CH₂Br 17-89 H O 1 H CH₃ CH₂CH═CH₂ 17-90 F O 1 H CH₃ CH₂CH═CH₂ 17-91 H O 1 H CH₃ CH(CH₃)CH═CH₂ 17-92 F O 1 H CH₃ CH(CH₃)CH═CH₂ 17-93 H O 1 H CH₃ CH₂CCl═CH₂ 17-94 F O 1 H CH₃ CH₂CCl═CH₂ 17-95 H O 1 H CH₃ CH₂C≡CH 17-96 F O 1 H CH₃ CH₂C≡CH 17-97 H O 1 H CH₃ CH(CH₃)C≡CH 17-98 F O 1 H CH₃ CH(CH₃)C≡CH 17-99 H O 1 H CH₃ CH₂CN 17-100  F O 1 H CH₃ CH₂CN

TABLE 242 X Z¹ n R¹ R⁴ R⁵ 17-101 H O 1 H CH₃ CH₂OCH₃ 17-102 F O 1 H CH₃ CH₂OCH₃ 17-103 H O 1 H CH₃ CH₂OC₂H₅ 17-104 F O 1 H CH₃ CH₂OC₂H₅ 17-105 H O 0 H — H 17-106 F O 0 H — H 17-107 H O 0 H — CH₃ 17-108 F O 0 H — CH₃ 17-109 H O 0 H — C₂H₅ 17-110 F O 0 H — C₂H₅ 17-111 H O 0 H — nC₃H₇ 17-112 F O 0 H — nC₃H₇ 17-113 H O 0 H — nC₄H₉ 17-114 F O 0 H — nC₄H₉ 17-115 H O 0 H — nC₅H₁₁ 17-116 F O 0 H — nC₅H₁₁ 17-117 H O 0 H — iC₃H₇ 17-118 F O 0 H — iC₃H₇ 17-119 H O 0 H — CH₂CH₂Cl 17-120 F O 0 H — CH₂CH₂Cl 17-121 H O 0 H — CH₂CH₂Br 17-122 F O 0 H — CH₂CH₂Br 17-123 H O 0 H — CH₂CH═CH₂ 17-124 F O 0 H — CH₂CH═CH₂ 17-125 H O 0 H — CH(CH₃)CH═CH₂

TABLE 243 X Z¹ n R¹ R⁴ R⁵ 17-126 F O 0 H — CH(CH₃)CH═CH₂ 17-127 H O 0 H — CH₂CCl═CH₂ 17-128 F O 0 H — CH₂CCl═CH₂ 17-129 H O 0 H — CH₂C≡CH 17-130 F O 0 H — CH₂C≡CH 17-131 H O 0 H — CH(CH₃)C≡CH 17-132 F O 0 H — CH(CH₃)C≡CH 17-133 H O 0 H — CH₂CN 17-134 F O 0 H — CH₂CN 17-135 H O 0 H — CH₂OCH₃ 17-136 F O 0 H — CH₂OCH₃ 17-137 H O 0 H — CH₂OC₂H₅ 17-138 F O 0 H — CH₂OC₂H₅ 17-139 H S 0 H — H 17-140 F S 0 H — H 17-141 H S 0 H — CH₃ 17-142 F S 0 H — CH₃ 17-143 H S 0 H — C₂H₅ 17-144 F S 0 H — C₂H₅ 17-145 H S 0 H — nC₃H₇ 17-146 F S 0 H — nC₃H₇ 17-147 H S 0 H — nC₄H₉ 17-148 F S 0 H — nC₄H₉ 17-149 H S 0 H — nC₅H₁₁ 17-150 F S 0 H — nC₅H₁₁

TABLE 244 X Z¹ n R¹ R⁴ R⁵ 17-151 H S 0 H — iC₃H₇ 17-152 F S 0 H — iC₃H₇ 17-153 H S 0 H — CH₂CH₂Cl 17-154 F S 0 H — CH₂CH₂Cl 17-155 H S 0 H — CH₂CH₂Br 17-156 F S 0 H — CH₂CH₂Br 17-157 H S 0 H — CH₂CH═CH₂ 17-158 F S 0 H — CH₂CH═CH₂ 17-159 H S 0 H — CH(CH₃)CH═CH₂ 17-160 F S 0 H — CH(CH₃)CH═CH₂ 17-161 H S 0 H — CH₂CCl═CH₂ 17-162 F S 0 H — CH₂CCl═CH₂ 17-163 H S 0 H — CH₂C≡CH 17-164 F S 0 H — CH₂C≡CH 17-165 H S 0 H — CH(CH₃)C≡CH 17-166 F S 0 H — CH(CH₃)C≡CH 17-167 H S 0 H — CH₂CN 17-168 F S 0 H — CH₂CN 17-169 H S 0 H — CH₂OCH₃ 17-170 F S 0 H — CH₂OCH₃ 17-171 H S 0 H — CH₂OC₂H₅ 17-172 F S 0 H — CH₂OC₂H₅ 17-173 H S 0 H — CH₂COOH 17-174 F S 0 H — CH₂COOH 17-175 H S 0 H — CH₂COOCH₃

TABLE 245 X Z¹ n R¹ R⁴ R⁵ 17-176 F S 0 H — CH₂COOCH₃ 17-177 H S 0 H — CH₂COOC₂H₅ 17-178 F S 0 H — CH₂COOC₂H₅ 17-179 H S 0 H — CH₂COOnC₃H₇ 17-180 F S 0 H — CH₂COOnC₃H₇ 17-181 H S 0 H — CH₂COOnC₄H₉ 17-182 F S 0 H — CH₂COOnC₄H₉ 17-183 H S 0 H — CH₂COOnC₅H₁₁ 17-184 F S 0 H — CH₂COOnC₅H₁₁ 17-185 H S 0 H — CH₂COOiC₃H₇ 17-186 F S 0 H — CH₂COOiC₃H₇ 17-187 H S 0 H — CH₂COOcC₅H₉ 17-188 F S 0 H — CH₂COOcC₅H₉ 17-189 H S 0 H — CH₂COOcC₆H₁₁ 17-190 F S 0 H — CH₂COOcC₆H₁₁ 17-191 H s 0 H — CH(CH₃)COOH 17-192 F S 0 H — CH(CH₃)COOH 17-193 H S 0 H — CH(CH₃)COOCH₃ 17-194 F S 0 H — CH(CH₃)COOCH₃ 17-195 H S 0 H — CH(CH₃)COOC₂H₅ 17-196 F S 0 H — CH(CH₃)COOC₂H₅ 17-197 H S 0 H — CH(CH₃)COOnC₃H₇ 17-198 F S 0 H — CH(CH₃)COOnC₃H₇ 17-199 H S 0 H — CH(CH₃)COOnC₄H₉ 17-200 F S 0 H — CH(CH₃)COOnC₄H₉

TABLE 246 X Z¹ n R¹ R⁴ R⁵ 17-201 H S 0 H — CH(CH₃)COOnC₅H₁₁ 17-202 F S 0 H — CH(CH₃)COOnC₅H₁₁ 17-203 H S 0 H — CH(CH₃)COOiC₃H₇ 17-204 F S 0 H — CH(CH₃)COOiC₃H₇ 17-205 H S 0 H — CH(CH₃)COOcC₅H₉ 17-206 F S 0 H — CH(CH₃)COOcC₅H₉ 17-207 H S 0 H — CH(CH₃)COOcC₆H₁₁ 17-208 F S 0 H — CH(CH₃)COOcC₆H₁₁

Compounds of the general formula:

TABLE 247 X R¹ R⁵ 20-1  H H CH₃ 20-2  F H CH₃ 20-3  Cl H CH₃ 20-4  H H C₂H₅ 20-5  F H C₂H₅ 20-6  Cl H C₂H₅ 20-7  H H nC₃H₇ 20-8  F H nC₃H₇ 20-9  Cl H nC₃H₇ 20-10 H H nC₄H₉ 20-11 F H nC₄H₉ 20-12 Cl H nC₄H₉ 20-13 H H iC₄H₉ 20-14 F H iC₄H₉ 20-15 Cl H iC₄H₉ 20-16 H H CH₂CH═CH₂ 20-17 F H CH₂CH═CH₂ 20-18 Cl H CH₂CH═CH₂ 20-19 H H CH(CH₃)CH═CH₂ 20-20 F H CH(CH₃)CH═CH₂ 20-21 Cl H CH(CH₃)CH═CH₂ 20-22 H H CH₂C≡CH 20-23 F H CH₂C≡CH 20-24 Cl H CH₂C≡CH 20-25 H H CH(CH₃)C≡CH

TABLE 248 X R¹ R⁵ 20-26 F H CH(CH₃)C≡CH 20-27 Cl H CH(CH₃)C≡CH

For some of the present compounds, their physical properties, i.e., melting points or data of ¹H-NMR (250 or 300 MHz, CDCl₃, TMS) in 6 (ppm), are shown as follows:

1-11 3.90-3.99 (2H, m), 4.10-4.18 (2H, m), 5.91 (1H, s), 7.50 (1H, dd, J=2.4, 8.7 Hz), 7.67 (H, d, J=8.7 Hz), 7.95 (1H, d, J=2.4 Hz)

1-218 m.p., 84.2° C.

1-376 m.p., 81.8° C.

1-382 m.p., 131.8° C.

1-388 m.p., 131.3° C.

1-424 m.p., 88.0° C.

1-430 1.22-1.29 (6H, m), 3.87-3.96 (2H, m), 4.07-4.17 (2H, m), 4.62 (2H, s), 5.11 (1H, m), 5.86 (1H, s), 6.87 (1H, d, J=6.2 Hz), 7.31 (1H, d,J=8.9 Hz)

1-634 m.p., 144.2° C.

1-688 m.p., 145.2° C.

1-760 3.65 (2H, s), 3.70 (3H, s), 3.94 (2H, t, J=8.9 Hz), 4.14 (2H, t, J=8.9 Hz), 5.87 (1H, s), 7.34 (1H, d, J=9.0 Hz), 7.47 (1H, d, J=7.3 Hz)

1-956 m.p., 135.8° C.

1-958 1.38 (3H, t, J=7.1 Hz), 3.91-3.98 (2H, m), 4.08-4.18 (2H, m), 4.37 (2H, q, J=7.1 Hz), 5.89 (1H, s), 7.37 (1H, d, J=9.3 Hz), 7.96 (1H, d, 7.7 Hz)

1-1094 3.31 (1H, dd, J=7.5, 14.0 Hz), 3.50 (1H, dd, J=7.5, 14.0 Hz), 3.74 (3H, s), 3.84-3.96 (2H, m), 4.06-4.16 (2H, m), 4.58 (1H, dd, J=7.5, 7.5 Hz), 5.87 (1H, s), 7.13-7.26 (2H, s), 7.44-7.53 (1H, m)

1-1252 m.p., 125.2° C.

6-5 m.p., 171.4° C.; decomposition

6-14 m.p., 177.0° C.; decomposition

6-23 m.p., 187.7° C.; decomposition

6-88 m.p., 230.5° C.; decomposition

6-100 m.p., 244.7° C.; decomposition

6-220 1.20-1.28 (3H, m), 1.50 (3H, d, J=6.9 Hz), 4.07 (1H, q, J=7.0 Hz), 4.15-4.24 (2H, m), 4.83-4.92 (1H, m), 6.56 (0.5H, s), 6.58 (0.5H, s), 6.68 (1H, d, J=3.2 Hz), 7.12-7.15 (1H, m), 7.23-7.25 (1H, m), 7.31 (1H, d, J=9.0 Hz)

6-310 3.19 (1H, ddt, J=15.4, 6.8, 1.3 Hz), 3.44 (1H, ddt, J=15.4, 6.2, 1.3 Hz), 4.77 (1H, ddd, J=17.0, 3.1, 1.3 Hz), 4.84 (1H, ddd, J=10.1, 3.1, 1.3 Hz), 5.69 (1H, dddd, J=17.0, 10.1, 6.8, 6.2 Hz), 6.68 (1H, s), 7.2-7.3 (2H, m)

6-340 m.p., 158.7° C.

6-346 1.71 (3H, d, J=7.5 Hz), 2.5-2.6 (1H, m), 4.7-4.9 (1H, m), 6.69 (1H, s), 7.1-7.2 (1H, m), 7.2-7.3 (2H, m), 7.38 (1H, d, J=10.8 Hz)

6-406 m.p., 108.3° C.

6-956 m.p., 134.2° C.

6-958 1.37 (3H, t, J=7.1 Hz), 4.38 (2H, q, J=7.1 Hz), 6.70 (1H, s), 7.15 (1H, d, J=2.0 Hz), 7.27 (1H, d, J=2.0 Hz), 7.45 (1H, d, J=9.3 Hz), 8.08 (1H, d, J=7.7 Hz)

6-980 m.p., 138.7° C.

6-1102 1.22-1.30 (3H, m), 3.28-3.60 (2H, m), 4.13-4.24 (2H, m), 4.54 (1H, t, J=7.5 Hz), 6.68 (0.5H, s), 6.69 (0.5H, s), 7.10-7.13 (1H, m), 7.25 (1H, d, J=2.0 Hz), 7.38-7.43 (2H, m)

7-26 m.p., 241.3° C.; decomposition

7-152 m.p., 210.9° C.

11-274 1.33-1.39 (6H, m), 3.89-3.97 (2H, m), 4.16-4.24 (2 H, m), 4.40-4.49 (1H, m), 5.83 (1H, s), 6.87 (1H, d, J=6.5 Hz), 7.28 (1H, d, J=8.9 Hz)

11-340 m.p., 131.7° C.

11-406 m.p., 97.5° C. 16-2 m.p., 189.6° C. 16-340 m.p., 162.9° C.

The following are formulation examples for the present compounds. In these example, the present compounds are designated by their compound numbers shown in Tables 1 to 248 and parts are by weight.

Formulation Example 1

Fifty parts of each of the present compounds 1-2, 1-32, 1-220, 1-262, 1-268, 1-274, 1-280, 1-340, 1-346, 1-376, 1-382, 1-388, 1-406, 1-424, 1-430, 1-460, 1-562, 1-634, 1-688, 1-712, 1-760, 1-956, 1-958, 1-1096, 2-26, 6-5, 6-23, 6-88, 6-100, 6-220, 6-274, 6-310, 6-316, 6-334, 6-340, 6-346, 6-406, 6-956, 6-958, 6-980, 6-1102, 7-26, 7-152,11-340, 11-406, 16-2, 16-274, and 16-340, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 45 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

Formulation Example 2

Ten parts of each of the present compounds 1-2, 1-32, 1-220, 1-262, 1-268, 1-274, 1-280, 1-340, 1-346, 1-376, 1-382, 1-388, 1-406, 1-424, 1-430, 1-460, 1-562, 1-634, 1-688, 1-712, 1-760, 1-956, 1-958, 1-1096, 2-26, 6-5, 6-23, 6-88, 6-100, 6-220, 6-274, 6-310, 6-316, 6-334, 6-340, 6-346, 6-406, 6-956, 6-958, 6-980, 6-1102, 7-26, 7-152,11-340, 11-406, 16-2, 16-274, and 16-340, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone are well mixed to give an emulsifiable concentrate for each compound.

Formulation Example 3

Two parts of the present compounds 1-2, 1-32, 1-220, 1-262, 1-268, 1-274, 1-280, 1-340, 1-346, 1-376, 1-382, 1-388, 1-406, 1-424, 1-430, 1-460, 1-562, 1-634, 1-688, 1-712, 1-760, 1-956, 1-958, 1-1096, 2-26, 6-5, 6-23, 6-88, 6-100, 6-220, 6-274, 6-310, 6-316, 6-334, 6-340, 6-346, 6-406, 6-956, 6-958, 6-980, 6-1102, 7-26, 7-152, 11-340, 11-406, 16-2, 16-274, and 16-340, 2 parts of synthetic hydrated silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 64 parts of kaolin clay are well pulverized and mixed. The mixture is well kneaded with the addition of water, and then granulated and dried to give a granule for each compound.

Formulation Example 4

Twenty-five parts of the present compounds 1-2, 1-32, 1-220, 1-262, 1-268, 1-274, 1-280, 1-340, 1-346, 1-376, 1-382, 1-388, 1-406, 1-424, 1-430, 1-460, 1-562, 1-634, 1-688, 1-712, 1-760, 1-956, 1-958, 1-1096, 2-26, 6-5, 6-23, 6-88, 6-100, 6-220, 6-274, 6-310, 6-316, 6-334, 6-340, 6-346, 6-406, 6-956, 6-958, 6-980, 6-1102, 7-26, 7-152, 11-340, 11-406, 16-2, 16-274, and 16-340, 50 parts of 10% aqueous polyvinyl alcohol solution, and 25 parts of water are mixed and then wet pulverized until the mean particle size comes to 5 μm or smaller to give a flowable for each compound.

Formulation Example 5

Five parts of the present compounds 1-2, 1-32, 1-220, 1-262, 1-268, 1-274, 1-280, 1-340, 1-346, 1-376, 1-382, 1-388, 1-406, 1-424, 1-430, 1-460, 1-562, 1-634, 1-688, 1-712, 1-760, 1-956, 1-958, 1-1096, 2-26, 6-5, 6-23, 6-88, 6-100, 6-220, 6-274, 6-310, 6-316, 6-334, 6-340, 6-346, 6-406, 6-956, 6-958, 6-980, 6-1102, 7-26, 7-152, 11-340, 11-406, 16-2, 16-274, and 16-340 is added to 40 parts of 10% aqueous polyvinyl alcohol solution and dispersed therein by emulsification with a homogenizer until the mean particle size comes to 10 μm or smaller, and 55 parts of water is added to give a thick emulsion for each compound.

The following test example will demonstrate that the present compounds are useful as the active ingredients of herbicides. In this example, the present compounds are designated by their compound numbers shown in Tables 1 to 248.

Test Example Foliar treatment on upland fields Cylindrical plastic pots each having a diameter of 10 cm and a depth of 10 cm were filled with soil and then seeded with ivyleaf morningglory (Ipomoea hederacea) and velvetleaf (Abutilon theophrasti). These test plants were grown in a greenhouse for 19 days. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2 and then diluted in its prescribed amount with water containing a spreading agent. The dilution was uniformly sprayed over the foliage of the test plants with a sprayer at a rate of 1000 liters per hectare After the application, the test plants were grown in the greenhouse for 7 days, and the herbicidal activity was examined. As a result, it was found that present compounds 1-2, 1-5, 1-14, 1-32, 1-88, 1-218, 1-220, 1-262, 1-268, 1-274, 1-280, 1-310, 1-340, 1-346, 1-370, 1-376, 1-382, 1-388, 1-406, 1-424, 1-430, 1-448, 1-454, 1-460, 1-514, 1-562, 1-634, 1-688, 1-706, 1-712, 1-760, 1-956, 1-958, 1-1094, 1-1096, 1-1246, 1-1252, 1-1255, 2-26, 6-5, 6-23, 6-88, 6-100, 6-220, 6-274, 6-310, 6-316, 6-334, 6-340, 6-346, 6-406, 6-956, 6-958, 6-980, 6-1102, 7-26, 7-152, 11-2, 11-274, 11-340, 11-406, 16-2, 16-274, and 16-340 made both test plants completely dead in a dosage of 500 g/ha. 

What is claimed is:
 1. A pyrimidinone derivative of the general formula:

wherein: R¹ is hydrogen or C₁-C₃ alkyl; R² is C₁-C₃ haloalkyl; R³ is nitrogen or CH; G is any group of the general formula:

wherein: E¹, E², E³, E⁴, E⁵, E⁶, E⁷, E⁸, E⁹, E¹⁰, E¹¹, and E¹² are independently hydrogen or C₁-C₃ alkyl; and Q is any group of the general formula:

wherein: X is hydrogen or halogen; Y is halogen, nitro, cyano, or trifluoromethyl; Z¹ is oxygen, sulfur, NH, or CH₂; n is 0 or 1; R⁴ is hydrogen or C₁-C₃ alkyl; R³ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, (C₃-C₈ cycloalkyl) C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₃ alkoxy C₁-C₃ alkoxy C₁-C₃ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, hydroxy C₁-C₆ alkyl, —CH₂CON(R¹²)R¹³, —CH₂COON(R¹²)R¹³,—CH(C₁-C₄ alkyl)CON(R¹²)R¹³, or —CH(C₁-C₄ alkyl)COON(R¹²)R¹³, wherein: R¹² and R¹³ are independently hydrogen, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy) carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₂-C₆ alkyl, (C₁-C₆ alkyl)carbonylamino C₂-C₆ alkyl, hydroxy C₂-C₆ alkyl, optionally substituted benzyl, optionally substituted phenyl, or {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, or R¹² and R¹³ are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene, or ethylenethioethylene; and B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR¹⁰, SR¹⁰, SO₂OR²¹, N(R¹²)R¹³, SO₂N(R¹²)R¹³,NR¹²(COR⁹), NR¹²(SO₂R²⁸), N(SO₂R²⁸)(SO₂R²⁹), N(SO₂R²⁸)(COR⁹), NHCOOR¹¹, CONR¹²R¹³, CSNR¹²R¹³,COR³⁰, CR²³═CR²⁴COR³⁰, CR²³═CR²⁴CON(R¹²)R¹³, CH₂CHWCON(R¹²)R¹³,CR³⁰═NOR³¹, CR³⁰═NN(R¹²)R¹³,CR³⁰(Z²R³²)₂, OCO₂R³², OCOR³², COOR²², CH₂OR¹⁰, CR²³═CR²⁴COOR²⁵, or CH₂CHWCOOR₂₅, wherein: R¹² and R¹³ are as defined above; W is hydrogen, chlorine, or bromine; Z² is oxygen or sulfur; R⁹ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl; R¹¹ is hydrogen, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl; R²⁸ and R²⁹ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, or phenyl; R³⁰ is hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, or C₃-C₆ alkynyl; R³¹ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)-carbonyl C₁-C₆ alkyl, or {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl; R³² is hydrogen, C₁-C₆ alkyl, C₃-Cs cycloalkyl, or C₃-C₆ alkenyl; R¹⁰ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)-carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkyl) C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl, —CH₂COON—(R¹²)R¹³, —CH(C₁-C₄ alkyl)COON(R¹²)R¹³, —CH₂CON(R¹²)R¹³, —CH(C₁-C₄ alkyl)CON(R¹²)R¹³ (wherein R¹² and R¹³ are as defined above), C₂-C₆ alkenyloxycarbonyl C₁-C₆ alkyl, C₃-C₆ haloalkenyloxycarbonyl C₁-C₆ alkyl, C₃-C₆ alkynyloxycarbonyl C₁-C₆ alkyl, C₃-C₆ haloalkynyloxycarbonyl C₁-C₆ alkyl, (C₁-C₆ alkylthio)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkylthio)-carbonyl C₁-C₆ alkyl, (C₃-C₆ alkenylthio)carbonyl C₁-C₆ alkyl, (C₃-C₆ haloalkenylthio)carbonyl C₁-C₆ alkyl, (C₃-C₆ alkynylthio)carbonyl C₁-C₆ alkyl, (C₃-C₆ haloalkynylthio)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkylthio)carbonyl C₁-C₆ alkyl, (C₃-C₈ cyclohaloalkylthio)carbonyl C₁-C₆ alkyl, ((C₃-C₈ cycloalkyl) C₁-C₆ alkylthio)carbonyl C₁-C₆ alkyl, di(C₁-C₆ alkyl)C═NO carbonyl C₁-C₆ alkyl, (optionally substituted benzylthio)-carbonyl C₁-C₆ alkyl, (optionally substituted phenylthio)-carbonyl C₁-C₆ alkyl, hydroxy C₂-C₆ alkoxycarbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₂-C₆ alkoxycarbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonylamino C₂-C₆ alkoxycarbonyl C₁-C₆ alkyl, {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₃-C₈ cycloalkoxycarbonyl, C₃-C₆ alkenyloxycarbonyl, optionally substituted benzyloxycarbonyl, C₁-C₆ alkylcarbonyl, optionally substituted benzyloxycarbonyl C₁-C₆ alkyl, optionally substituted phenoxycarbonyl C₁-C₆ alkyl, optionally substituted furyloxycarbonyl C₁-C₆ alkyl, optionally substituted furyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted thienyloxycarbonyl C₁-C₆ alkyl, optionally substituted thienyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrrolyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrrolyloxy C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted imidazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted imidazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyrazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted thiazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted thiazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted oxazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted oxazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted isothiazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted isothiazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted isoxazoyloxycarbonyl C₁-C₆ alkyl, optionally substituted isoxazoyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyradinyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyradinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyriaidinyloxy carbonyl C₁-C₆ alkyl, optionally substituted pyrimidinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridazinyloxycarbonyl C₁-C₆ alkyl, optionally substituted pyridazinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolidinyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolidinyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolyloxycarbonyl C₁-C₆ alkyl, optionally substituted indolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted indazolyloxycarbonyl C₁-C₆ alkyl, optionally substituted indazolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted quinolyloxycarbonyl C₁-C₆ alkyl, optionally substituted quinolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, optionally substituted isoquinolyloxycarbonyl C₁-C₆ alkyl, or optionally substituted isoquinolyl C₁-C₆ alkyloxycarbonyl C₁-C₆ alkyl, or a group of the general formula:

wherein: R¹⁴ is hydrogen or C₁-C₅ alkyl; and R¹⁵ is hydrogen, hydroxyl, or a group of —O—COR¹⁶, wherein: R¹⁶ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₈ cycloalkyl, optionally substituted phenyl, optionally substituted benzyl, or C₁-C₆ alkoxy; or a group of the general formula:

wherein: R¹⁷ is hydrogen, halogen, or C₁-C₆ alkyl; and R¹⁸ is C₃-C₈ cycloalkyl, benzyl, C₂-C₁₀ alkyl with an epoxy group, C₃-C₈ cycloalkyl C₁-C₆ alkyl, C₃-C₈ cycloalkyl C₂-C₆ alkenyl, carboxy C₂-C₆ alkenyl, (C₁-C₈ alkoxy)carbonyl C₂-C₆ alkenyl, (C₁-C₈ haloalkoxy)carbonyl C₂-C₆ alkenyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₂-C₆ alkenyl, (C₃-C₈ cycloalkoxy)-carbonyl C₂-C₆ alkenyl, C₁-C₆ alkyl substituted with OR¹⁹ and OR²⁰ on the same carbon atom, C₂-C₆ alkenyl substituted with OR¹⁹ and OR²⁰ on the same carbon atom, C₁-C₆ alkyl substituted with SR¹⁹ and SR²⁰ on the same carbon atom, or C₂-C₆ alkenyl substituted with SR¹⁹ and SR²⁰ on the same carbon atom, wherein: R¹⁹ and R²⁰ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, or R¹⁹ and R²⁰ are taken together to form ethylene optionally substituted with halogen, trimethylene optionally substituted with halogen, tetramethylene optionally substituted with halogen, pentamethylene optionally substituted with halogen, or ethyleneoxyethylene optionally substituted with halogen; R²¹ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-Cs cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, or benzyl; R²² is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)-carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkyl, {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, hydroxy C₁-C₆ alkyl, —CH₂-COON(R²⁶)R²⁷, —CH(C₁-C₄ alkyl) COON(R²⁶)R²⁷, —CH₂CON—(R²⁶)R²⁷, or —CH(C₁-C₄ alkyl)CON(R²⁶)R²⁷, wherein: R²⁶ and R²⁷ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₁-C₄ alkoxy C₁-C₄ alkyl, C₁-C₄ alkylthio C₁-C₄ alkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)-carbonyl C₁-C₆ alkyl, or {(C₁-C₄ alkoxy) C₁-C₄ alkyl}-carbonyl C₁-C₆ alkyl, or R²⁶ and R²⁷ are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene; R²³ and R²⁴ are independently hydrogen or C₁-C₆ alkyl; and R²⁵ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl.
 2. The pyrimidinone derivative according to claim 1, wherein Q is Q-1.
 3. The pyrimidinone derivative according to claim 1, wherein Q is Q-2.
 4. The pyrimidinone derivative according to claim 1, wherein Q is Q-5.
 5. The pyrimidinone derivative according to claims 1 to 4, wherein R³ is nitrogen.
 6. The pyrimidinone derivative according to claims 1 to 4, wherein R³ is CH.
 7. The pyrimidinone derivative according to claims 1 to 6, wherein G is G-1.
 8. The pyrimidinone derivative according to claims 1 to 6, wherein G is G-3.
 9. The pyrimidinone derivative according to claims 1 to 8, wherein R² is trifluoromethyl.
 10. The pyrimidinone derivative according to claims 1 to 8, wherein R² is chlorodifluoromethyl.
 11. A herbicide comprising a pyrimidinone derivative according to claim 1, and an inert carrier or diluent.
 12. A method for controlling weeds, which comprises applying a pyrimidinone derivative according to claim 1 to an area where the weeds grow or will grow.
 13. A compound selected from the group consisting of 7-Fluoro-6-[7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzo~xadin-3-one 6-[7-Oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one 6-Fluoro-5-[7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydrbimidazo[1,2-a]-pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one 6-[7-Oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one 8-(4-Chloro-2-fluoro-5-methoxyphenyl)-5-trifluoromethyl-2, 3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one 8-(4-Chloro-2-fluoro-5-ethoxyphenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one 8-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one 8-(4-Chloro -2-fluoro-5-prop argyloxyphenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one 8-(4-Chloro-2-fluoro-5-(1-methylpropargyloxy)phenyl)-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7-one {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3,7, 8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid methyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3,7, 8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy} acetic acid ethyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid isopropyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo.5-trifluoromethyl-2,3, 7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid methyl ester 2-(2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy~propionic acid ethyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid isopropyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid methyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid ethyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3, 7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid methyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid ethyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid methyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3, 7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid ethyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3, 7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid methyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid ethyl ester N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenyl}methanesulfonamide N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)phenyl}chloromethanesulfonamide, N-{2-Chloro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo-[1,2-a]pyrimidin-8-yl)phenyl}methanesulfonamide 2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3,7,8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)benzoic acid methyl ester 2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-2, 3,7, 8-tetrahydroimidazo[1,2-a]pyrimidin-8-yl)benzoic acid ethyl ester 2-Chloro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid methyl ester 2-Chloro-5-(7-oxo-5-trifluoromethyl-2,3,7,8-tetrahydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid ethyl ester 7-Fluoro-6-[7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one 6-[7-Oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-4-propargyl-3,4-dihydro-2H-1,4-benzoxadin-3-one 6-Fluoro-5-[7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one 5-[7-Oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-8-yl]-3-propargyl-2,3-dihydro-1,3-benzothiazol-2-one 8-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-7-one 8-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-7-one 8-(4-Chloro-2-fluoro-5-(1-methylpropargyloxy)phenyl)-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]pyrimidin-7-one {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid methyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid ethyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}acetic acid isopropyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid methyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid ethyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenoxy}propionic acid isopropyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid methyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}acetic acid ethyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid methyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylthio}propionic acid ethyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid methyl ester {2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}acetic acid ethyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid methyl ester 2-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenylamino}propionic acid ethyl ester N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenyl}methanesulfonamide N-{2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)phenyl}chloromethanesulfonamide N-{2-Chloro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]-pyrimidin-8-yl)phenyl}methanesulfonamide 2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)benzoic acid methyl ester 2-Chloro-4-fluoro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo-[1,2-a]pyrimidin-8-yl)benzoic acid ethyl ester 2-Chloro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid methyl ester 2-Chloro-5-(7-oxo-5-trifluoromethyl-7,8-dihydroimidazo[1,2-a]-pyrimidin-8-yl)benzoic acid ethyl ester. 